xoth.publishing
Swords against tentacles!
Adding levels to checks is generally not done in 5E, and it breaks Bounded Accuracy. Also, any chance to actually use skills is good.When I tried to make ship rules, one thing I ended up doing was adding the character level of the officer to a lot of checks.
This ensures that high-level PCs are useless just because they lack skills. And a level 10 barbarian can help a lot as a gunnery officer, even if they don't know guns.
Do consider week-long long rests, and only long rests when it is safe. Any kind of extended travel campaign instantly becomes better if you do it.
It does mean you have to adapt threats. With week long rests, the power of a PC party isn't nearly as high as with nightly ones, because retreat and regroup to do a long rest means "surrender" when you give the opposing side a full weak off.
Only long rests when it is safe is part of this rule. Week-long long rests could be used if you opt for more "realism".
I'd do two things.
First, I'd add in some "supplies" and "crew", "morale" and "speed" stats for my ship. And have most events consume supplies, lose crew, gain/lose morale, reduce/increase speed.
The destination is "distance" units away, where a "typical" day you move "speed".
Next, get a HUGE table of random ocean events. Most of them are innocuous. Like 100+.
This is too complicated for what I'm trying to do here.
Also, consider having checks be triggered by events, instead of "everyone does a check, then we determine events".
Like, you don't make a captain check until there is a potential mutiny. It makes the check have higher stakes. The officer checks act sort of like saving throws, instead of busy-rolls.
I like that it would raise stakes to roll the checks after the event, and reduce busy-rolls. However, with the way I've set up the events table, you always want to roll the checks to see if you can improve the result to get a benefit (in the 16-20 range), so I don't see how the number of rolls could be reduced. But switching around the order of the rolls (event, then checks) would probably be an improvement, yes.