Jaager

Theory here:
 
It is difficult to get an acceptable finish on a gunport by cutting it and finishing the sides of the cut.
It may be a successful procedure to make the opening oversize and inserting a frame of a sill and lintel and having a veneer layer where the frame timbers would be.
If you are set on all rectangular openings, the same jig can be used for every port on a particular deck to glue up the framing.  It is then a matter of shimming each frame.  If the frames are mounted before placing the outside planking, .....
 

An aspect of gunports that seems to be often missed:
The sides of the ports are parallel to the frames, not perpendicular to the LWL.
The sills and lintels are parallel to the deck at the port location.  In the middle there is little or no difference port to port.  At the ends, each port is individual in shape.
The ports are parallelograms with vertical sides.  A stick used as a gauge for every port on a particular deck produces an inauthentic result.
The gun truck or skid sits on the deck.  The barrel tracks parallel to the deck.

I am just speculating, but  Old Brown and Franklin hide glues are convenient because they are used at room temp.  The downside is that the water concentration has to be high enough to produce unwanted side effects in the wood being glued.   If you are serious, you might oughta pay the price of the hassle of a glue pot.   The water concentration is just enough to get a fluid - if you do it correctly.
I break my rules this one time and use a man made synthetic -PVA  - because a hot pot is too much extra work.

The foundational cause lays with OcCre for supplying you with a crap wood species to begin with. 
I would place a serious bet on Walnut being the among most available of the various shades of both wood dyes and wood stains on the market.
The shade is easy to get without having to use a wood species that is open pore and looks fuzzy and is brittle to bote.  What is more inappropriate is that none of the species of wood commonly used to build a ships is anything like Walnut in color.  The same situation occurs with decks.  No wood used for decking is near as white as Holly.  This is not a factor with mass market kits.  They use economy species for hull planking, so no way would they afford the cost of Holly.  (I am addressing the American Ilex opaca - harvested in Winter and immediately kiln dried - great for marquetry -  English Holly Ilex aquafolium is plenty yellow enough to stand for Pine or Oak.)
 
I get the humor -but   -   as a way to spend your time -
Wood has no consciousness.  There is nothing to beat - except chemistry/physics/Nature - where,  is most cases - even if you win - you actually lose. 

The foundational cause lays with OcCre for supplying you with a crap wood species to begin with. 
I would place a serious bet on Walnut being the among most available of the various shades of both wood dyes and wood stains on the market.
The shade is easy to get without having to use a wood species that is open pore and looks fuzzy and is brittle to bote.  What is more inappropriate is that none of the species of wood commonly used to build a ships is anything like Walnut in color.  The same situation occurs with decks.  No wood used for decking is near as white as Holly.  This is not a factor with mass market kits.  They use economy species for hull planking, so no way would they afford the cost of Holly.  (I am addressing the American Ilex opaca - harvested in Winter and immediately kiln dried - great for marquetry -  English Holly Ilex aquafolium is plenty yellow enough to stand for Pine or Oak.)
 
I get the humor -but   -   as a way to spend your time -
Wood has no consciousness.  There is nothing to beat - except chemistry/physics/Nature - where,  is most cases - even if you win - you actually lose. 

The foundational cause lays with OcCre for supplying you with a crap wood species to begin with. 
I would place a serious bet on Walnut being the among most available of the various shades of both wood dyes and wood stains on the market.
The shade is easy to get without having to use a wood species that is open pore and looks fuzzy and is brittle to bote.  What is more inappropriate is that none of the species of wood commonly used to build a ships is anything like Walnut in color.  The same situation occurs with decks.  No wood used for decking is near as white as Holly.  This is not a factor with mass market kits.  They use economy species for hull planking, so no way would they afford the cost of Holly.  (I am addressing the American Ilex opaca - harvested in Winter and immediately kiln dried - great for marquetry -  English Holly Ilex aquafolium is plenty yellow enough to stand for Pine or Oak.)
 
I get the humor -but   -   as a way to spend your time -
Wood has no consciousness.  There is nothing to beat - except chemistry/physics/Nature - where,  is most cases - even if you win - you actually lose. 

Someone earns credit for a clever but very cynical marketing hook.   It is designed to mislead a distracted tourist into confusing prisoner with POW. 
It would be as good as license plates, except ready access to small sharp tools may not be all that wise in a convict population.  The actual shop may be a boiler room or sweatshop environment, so feeling like being a prisoner fits.  
 
As for the Morgan,  the use of totally inappropriate species of wood is blindingly obvious.  Would that prospective kit buyers could see it.

Someone earns credit for a clever but very cynical marketing hook.   It is designed to mislead a distracted tourist into confusing prisoner with POW. 
It would be as good as license plates, except ready access to small sharp tools may not be all that wise in a convict population.  The actual shop may be a boiler room or sweatshop environment, so feeling like being a prisoner fits.  
 
As for the Morgan,  the use of totally inappropriate species of wood is blindingly obvious.  Would that prospective kit buyers could see it.

It is a personal source of irritation, but asking about what is the "best" of anything much outside a bar or chatroom is pointless.  It is of no use here.  Asking about what is "excellent" or "necessary" or "a good value" will yield valuable information - if the subject is relevant to this site's purpose.
 
I am going to make propositions rather than suggestions given the scant clues offered by the OP:
 
The nature of the inquiry suggests that the OP is a beginner and is building a kit or intends to.  The question does not say what is to be cut.  
Remembering back to my Yellow Box, solid hull days, even with the high degree of semi scratch fabrication there was little that required more that the occasional use of a narrow blade razor saw.
From what I can see of it, neither old style nor recent laser cut kits require much sawing.  Any sort of "saw kit" will be mostly bench clutter.  The $12 plastic sprue that @Bob Cleek has found for us has no downside even if nothing comes up that requires its use.
I think that serious saw use comes with scratch.  Then, the jobs will dictate the sort of saw needed.   With that narrow class, asking here about which saws in it are junk and which are value may save money and frustration.
 
 
I agree with @von_bednar that the Japanese mini pull cut saws are easier for me to cross cut   ~1/4" thick stock or similar.  Many of the saw models have no back support -a pull cut does not need it - but the push reset needs care less the blade be kinked  -  There are choices in tooth length and set.  Wide thick stock being cut with a saw with little or no set saves on kerf, but the wood wants to seize the blade. Usually, with a crosscut, kerf  is not a factor worth factoring in.
 

It is a personal source of irritation, but asking about what is the "best" of anything much outside a bar or chatroom is pointless.  It is of no use here.  Asking about what is "excellent" or "necessary" or "a good value" will yield valuable information - if the subject is relevant to this site's purpose.
 
I am going to make propositions rather than suggestions given the scant clues offered by the OP:
 
The nature of the inquiry suggests that the OP is a beginner and is building a kit or intends to.  The question does not say what is to be cut.  
Remembering back to my Yellow Box, solid hull days, even with the high degree of semi scratch fabrication there was little that required more that the occasional use of a narrow blade razor saw.
From what I can see of it, neither old style nor recent laser cut kits require much sawing.  Any sort of "saw kit" will be mostly bench clutter.  The $12 plastic sprue that @Bob Cleek has found for us has no downside even if nothing comes up that requires its use.
I think that serious saw use comes with scratch.  Then, the jobs will dictate the sort of saw needed.   With that narrow class, asking here about which saws in it are junk and which are value may save money and frustration.
 
 
I agree with @von_bednar that the Japanese mini pull cut saws are easier for me to cross cut   ~1/4" thick stock or similar.  Many of the saw models have no back support -a pull cut does not need it - but the push reset needs care less the blade be kinked  -  There are choices in tooth length and set.  Wide thick stock being cut with a saw with little or no set saves on kerf, but the wood wants to seize the blade. Usually, with a crosscut, kerf  is not a factor worth factoring in.
 

It is a personal source of irritation, but asking about what is the "best" of anything much outside a bar or chatroom is pointless.  It is of no use here.  Asking about what is "excellent" or "necessary" or "a good value" will yield valuable information - if the subject is relevant to this site's purpose.
 
I am going to make propositions rather than suggestions given the scant clues offered by the OP:
 
The nature of the inquiry suggests that the OP is a beginner and is building a kit or intends to.  The question does not say what is to be cut.  
Remembering back to my Yellow Box, solid hull days, even with the high degree of semi scratch fabrication there was little that required more that the occasional use of a narrow blade razor saw.
From what I can see of it, neither old style nor recent laser cut kits require much sawing.  Any sort of "saw kit" will be mostly bench clutter.  The $12 plastic sprue that @Bob Cleek has found for us has no downside even if nothing comes up that requires its use.
I think that serious saw use comes with scratch.  Then, the jobs will dictate the sort of saw needed.   With that narrow class, asking here about which saws in it are junk and which are value may save money and frustration.
 
 
I agree with @von_bednar that the Japanese mini pull cut saws are easier for me to cross cut   ~1/4" thick stock or similar.  Many of the saw models have no back support -a pull cut does not need it - but the push reset needs care less the blade be kinked  -  There are choices in tooth length and set.  Wide thick stock being cut with a saw with little or no set saves on kerf, but the wood wants to seize the blade. Usually, with a crosscut, kerf  is not a factor worth factoring in.
 

It is a personal source of irritation, but asking about what is the "best" of anything much outside a bar or chatroom is pointless.  It is of no use here.  Asking about what is "excellent" or "necessary" or "a good value" will yield valuable information - if the subject is relevant to this site's purpose.
 
I am going to make propositions rather than suggestions given the scant clues offered by the OP:
 
The nature of the inquiry suggests that the OP is a beginner and is building a kit or intends to.  The question does not say what is to be cut.  
Remembering back to my Yellow Box, solid hull days, even with the high degree of semi scratch fabrication there was little that required more that the occasional use of a narrow blade razor saw.
From what I can see of it, neither old style nor recent laser cut kits require much sawing.  Any sort of "saw kit" will be mostly bench clutter.  The $12 plastic sprue that @Bob Cleek has found for us has no downside even if nothing comes up that requires its use.
I think that serious saw use comes with scratch.  Then, the jobs will dictate the sort of saw needed.   With that narrow class, asking here about which saws in it are junk and which are value may save money and frustration.
 
 
I agree with @von_bednar that the Japanese mini pull cut saws are easier for me to cross cut   ~1/4" thick stock or similar.  Many of the saw models have no back support -a pull cut does not need it - but the push reset needs care less the blade be kinked  -  There are choices in tooth length and set.  Wide thick stock being cut with a saw with little or no set saves on kerf, but the wood wants to seize the blade. Usually, with a crosscut, kerf  is not a factor worth factoring in.
 

It is a personal source of irritation, but asking about what is the "best" of anything much outside a bar or chatroom is pointless.  It is of no use here.  Asking about what is "excellent" or "necessary" or "a good value" will yield valuable information - if the subject is relevant to this site's purpose.
 
I am going to make propositions rather than suggestions given the scant clues offered by the OP:
 
The nature of the inquiry suggests that the OP is a beginner and is building a kit or intends to.  The question does not say what is to be cut.  
Remembering back to my Yellow Box, solid hull days, even with the high degree of semi scratch fabrication there was little that required more that the occasional use of a narrow blade razor saw.
From what I can see of it, neither old style nor recent laser cut kits require much sawing.  Any sort of "saw kit" will be mostly bench clutter.  The $12 plastic sprue that @Bob Cleek has found for us has no downside even if nothing comes up that requires its use.
I think that serious saw use comes with scratch.  Then, the jobs will dictate the sort of saw needed.   With that narrow class, asking here about which saws in it are junk and which are value may save money and frustration.
 
 
I agree with @von_bednar that the Japanese mini pull cut saws are easier for me to cross cut   ~1/4" thick stock or similar.  Many of the saw models have no back support -a pull cut does not need it - but the push reset needs care less the blade be kinked  -  There are choices in tooth length and set.  Wide thick stock being cut with a saw with little or no set saves on kerf, but the wood wants to seize the blade. Usually, with a crosscut, kerf  is not a factor worth factoring in.
 

It is a personal source of irritation, but asking about what is the "best" of anything much outside a bar or chatroom is pointless.  It is of no use here.  Asking about what is "excellent" or "necessary" or "a good value" will yield valuable information - if the subject is relevant to this site's purpose.
 
I am going to make propositions rather than suggestions given the scant clues offered by the OP:
 
The nature of the inquiry suggests that the OP is a beginner and is building a kit or intends to.  The question does not say what is to be cut.  
Remembering back to my Yellow Box, solid hull days, even with the high degree of semi scratch fabrication there was little that required more that the occasional use of a narrow blade razor saw.
From what I can see of it, neither old style nor recent laser cut kits require much sawing.  Any sort of "saw kit" will be mostly bench clutter.  The $12 plastic sprue that @Bob Cleek has found for us has no downside even if nothing comes up that requires its use.
I think that serious saw use comes with scratch.  Then, the jobs will dictate the sort of saw needed.   With that narrow class, asking here about which saws in it are junk and which are value may save money and frustration.
 
 
I agree with @von_bednar that the Japanese mini pull cut saws are easier for me to cross cut   ~1/4" thick stock or similar.  Many of the saw models have no back support -a pull cut does not need it - but the push reset needs care less the blade be kinked  -  There are choices in tooth length and set.  Wide thick stock being cut with a saw with little or no set saves on kerf, but the wood wants to seize the blade. Usually, with a crosscut, kerf  is not a factor worth factoring in.
 

Even if the wedges were not used to fix the rake of the mast - and I cannot imagine allowing a mast to careen around at the partners,  unless the crew wanted to take showers at the masts on the lower deck(s), something like wedges would be needed to stop rain water or seawater overwash from flooding at the mast-deck gap.  Tightly bound tarred canvas is what I understand covered the wedges on the weather exposed decks.  
Thinking about it, on multi-decked ships, wedges with no covering in place on every deck would serve to spread out the point of force transfer from the spars to the hull.

Siggi,
 
With your obvious superb skill at painting at miniature scale,  would it not be easier to faux paint the bricks. 
What you have is absolutely authentic.  Actual masonry at scale must be tedious and frustrating. 
The brick making -  maybe interesting to do ONCE - just to say you did it - but so many small parts really  asks a lot of an adhesive over time.
 
Using oil base paint, a pallet to get different shades of red clay - add in a bit of pumice for the dulling - lots of narrow masking tape strips.....
 
What you are doing is an impressive experiment,  but will the extra time and work be worth the result vs using a faux representation?

Even if the wedges were not used to fix the rake of the mast - and I cannot imagine allowing a mast to careen around at the partners,  unless the crew wanted to take showers at the masts on the lower deck(s), something like wedges would be needed to stop rain water or seawater overwash from flooding at the mast-deck gap.  Tightly bound tarred canvas is what I understand covered the wedges on the weather exposed decks.  
Thinking about it, on multi-decked ships, wedges with no covering in place on every deck would serve to spread out the point of force transfer from the spars to the hull.

If you read  the top chapter in the New Member Introductions forum:  For Beginners -- A Cautionary Tale
and take seriously the suggestions re:  beginner kits  you stand a good chance of achieving your goal and promise.
 
Wooden model shipbuilding is unlike other categories of scale modeling.  It has a unique nomenclature /language  that is not huge, but necessary to know.
The subjects represent the height and breadth of the technical and engineering achievements  of their civilization.
Wood requires familiarity with a range of tools - it is not assemble and paint.
Being overwhelmed, frustrated, loosing inspiration is very common - about a rule - almost a law - all is not lost when it hits,  you just wait it out and come back with batteries recharged.
If too complex a subject is a first subject - most often,that first negative wave kills any desire to return.

Siggi,
 
With your obvious superb skill at painting at miniature scale,  would it not be easier to faux paint the bricks. 
What you have is absolutely authentic.  Actual masonry at scale must be tedious and frustrating. 
The brick making -  maybe interesting to do ONCE - just to say you did it - but so many small parts really  asks a lot of an adhesive over time.
 
Using oil base paint, a pallet to get different shades of red clay - add in a bit of pumice for the dulling - lots of narrow masking tape strips.....
 
What you are doing is an impressive experiment,  but will the extra time and work be worth the result vs using a faux representation?

Siggi,
 
With your obvious superb skill at painting at miniature scale,  would it not be easier to faux paint the bricks. 
What you have is absolutely authentic.  Actual masonry at scale must be tedious and frustrating. 
The brick making -  maybe interesting to do ONCE - just to say you did it - but so many small parts really  asks a lot of an adhesive over time.
 
Using oil base paint, a pallet to get different shades of red clay - add in a bit of pumice for the dulling - lots of narrow masking tape strips.....
 
What you are doing is an impressive experiment,  but will the extra time and work be worth the result vs using a faux representation?

Masa,
 
Looking at your printing.   For 1:120 down to 1:192   I am seeing the use of a loom to hold the foot ropes tightly and at scale intervals.  a kinda   wide loom  - soak the shroud lines with clear pH7 PVA  and lay them (under tension) across the foot ropes to bond and cut free when set. 
 
I suspect that the properties of the plastic (that make it able to be melted and squirted and then adhere to previous dried plastic and solidify quickly)   will also make it more likely to continue its polymerization reaction when exposed to ambient UV and oxygen to a point of becoming a brittle powder in a short time interval.   I think this is the eventual fate of most plastics.  But the rate of continuing reaction varies widely and some may last as long as 100 years or more.  I am betting that what 3D printing material will show is 10 years at best - and the thinner it is, the shorter will be its half life. 

Using either to do the job of a plane will probably not be a rewarding experience.  A plane is designed to limit the depth of cut.
 
The hounds region is usually smaller than the round.   Use the mast required square as the chucked section and after the rounding, work the square section down to the correct square/ rectangular cross section.  
I would probably use the top of my vise jaws as my depth stop.
 
As for your "Would that work?" question:  i.e.  hand planing to octagonal ( or whatever a 16 sided polygon is named) and then sanding  vs starting with a square and using a sanding function to do all of the cutting,
(putting on my professor hat) =  start with two identical sticks - make your mast using a plane on one and use the drill as a lathe and use a sanding stick as a very shallow cutting turning chisel on the other and give us the result of your experiment.    My imagination tells me that using a sanding stick (lots of sanding sticks probably) will take significantly longer?

I keep coming back to the thought that laying the deck would be a much more satisfying experience were you using an appropriate species of wood, instead of the junk species Anigre.
 
One concept to take to heart is that with a wooden ship of the age of sail = there are seldom two timbers that are identical.  There are mirror images.  Dutch ships in the deadflat may be an exception for a long stretch.  Galleys perhaps. 

Masa,
 
Looking at your printing.   For 1:120 down to 1:192   I am seeing the use of a loom to hold the foot ropes tightly and at scale intervals.  a kinda   wide loom  - soak the shroud lines with clear pH7 PVA  and lay them (under tension) across the foot ropes to bond and cut free when set. 
 
I suspect that the properties of the plastic (that make it able to be melted and squirted and then adhere to previous dried plastic and solidify quickly)   will also make it more likely to continue its polymerization reaction when exposed to ambient UV and oxygen to a point of becoming a brittle powder in a short time interval.   I think this is the eventual fate of most plastics.  But the rate of continuing reaction varies widely and some may last as long as 100 years or more.  I am betting that what 3D printing material will show is 10 years at best - and the thinner it is, the shorter will be its half life. 

Siggi,
 
With your obvious superb skill at painting at miniature scale,  would it not be easier to faux paint the bricks. 
What you have is absolutely authentic.  Actual masonry at scale must be tedious and frustrating. 
The brick making -  maybe interesting to do ONCE - just to say you did it - but so many small parts really  asks a lot of an adhesive over time.
 
Using oil base paint, a pallet to get different shades of red clay - add in a bit of pumice for the dulling - lots of narrow masking tape strips.....
 
What you are doing is an impressive experiment,  but will the extra time and work be worth the result vs using a faux representation?