Sword of Spirit
Legend
I couldn't help myself: More Ships of the Sea
Looks awesome!
Two questions:
1) Were the ship lengths determined in reference to the sailing ship's listed length of 100', or it's actual deck plan length of 80'? (The deck plan is likely the correct value, since the warship is supposed to be larger, and it has 100' for both it's listed length and it's actual deck plan.)
2) Was the Strength of 20 for the sloop intentional? It seems odd for such a small ship to have higher strength than most of the larger ships.
Great questions!
1. My intention was that the sloop statistics would handle all small sailboats of this type (even though many such sailboats are technically not "sloops"). It's like how you can use the statistics for a glaive to represent a wide variety of polearms.
If we want to differentiate ships further, we can do it with minor tweaks, rather than entirely new stat blocks. You know how some monsters in the Monster Manual have sidebars with variations? The swarm of insects is a good example: you can turn it into a spider swarm, wasp swarm, etc. just by adding or removing a few traits. So if a cutter is substantially different than a sloop, we could have a sidebar that says something like, "Cutter: Reduce the passenger capacity to 1, decrease the hit points to 50, and increase the speed to 35 feet." (I am just making those stats up: I don't really know how a cutter, or any other pilot ship, differs from other small sailboats. Although I do suspect that it doesn't need to be super "fast" because I'm guessing most ships don't come racing into the harbor at top speed.)
Definitely going with sidebars for variants is the right call. It follows 5e patterns and keeps the material more manageable.
2. For turning radius: My favorite system for this that I've ever seen was Star Wars d20 Revised. Every ship had the exact same turning radius, acceleration, etc. But you could overcome those limitations with a piloting check, and each ship had a maneuverability modifier to this check. I love it because it was very easy to remember (each ship gets a number -- a modifier -- instead of a new set of turning rules) and because it was extremely flexible (any wacky move a pilot wanted to try -- it was way easier to do with a tie fighter than a star destroyer).
For ships, I'm planning to adopt a similar system. Simply applying the ship's Dexterity modifier to such checks would be good, except that ships have very little variation in their Dex mods (they cluster tightly around -3). It make sense to base these checks on the ship's length, since longer ships should be harder to turn, and ship lengths are generally multiples of 20 (DC 5 per 20 feet of length works well). Or, we could give some ships a special trait, probably as part of the helm/tiller: "Maneuverable. When you make an ability check or saving throw for this ship to turn sharply, avoid an obstacle, change its speed suddenly, or perform a similar fancy nautical maneuver, you make the check or save with advantage."
What makes the most sense to everybody else? I'm really trying to avoid "retconning" the statistics from Ghosts of Saltmarsh, but I'm open to doing that as a variant/optional thing, if it works.
I'd absolutely go with the route of least changes. A special trait seems like the way to go here. 5e play assumptions would already imply that the DM might be doing things like asking for ability checks (and applying water vehicle proficiency where applicable) to exert fine control over ship movements, so a trait that gives a bonus if that is happening works well and doesn't add any additional design space layering.