Questions

[Stella Ruby]

I did Barbosa's training and afterward my pistol was not in my weapons menu and nothing showed under f2 but I was able to shoot with it.
I went to the blacksmith and purchased the starter pistol and was then able to equip it in f2 and also gain points when using it. I have used it successfully on crabs, skeletons, and alligators.
You can purchase a new cutlass from the blacksmith, one of the first townspeople on Port Royal if you enter the town furtherst from the half-ship. You won't be able to use it until your cutlass is a level five, but you can purchase it before hand and have it ready when you level up.
This has been my experience.

[searage]

eventually, all pirates get bugged so the weapon screen comes up empty and at that point you are forever stuck with whatever weapons you had assigned to F1-F4.

so when starting a new character, you should do your best to obtain and equip whatever weapons you want to have the very first thing.