@Levis
Confirmed bug, and I think figured out what is going on. It seems to depend on starting ship selection.
1st batch of Tests: Ran multiple gambler starts under various conditions. If the starting boat was an armed tartane or a tier 6 ship, then there was no bug, I got the dialogue about winning the boat, everything worked.
2nd batch of Tests: Twice with starting boat as a dinghy, the bug occurred, and instead of the gambler dialogue you get the standard tutorial dialogue about the captain giving you the ship and retiring. Then, if you select stormy start, the gambler start picks up on the beech, and you have the inconsistency bug I mentioned.
So, I think this bug might occur when the player's starting ship selection does not have a captain's cabin (I am not sure if ships other than the Dinghy are that small, it might be confined to it), and the normal gambler start bugs out without a proper cabin to put the player in, and the normal tutorial takes over.
Although the bug is there, it probably is not worth it to spend time to fix this bug--I don't think many players choose to have such a small ship on a gambler start. Basically, I was trying to replicate the castaway start with another role, but I went back to castaway anyway.