Managed to get negative debt in the dice game, which could accrue as high (low?) as I wanted. Got it up to -10,000 debt, then "paid" it off for a gain of 10,000 gold. I'm sure this has been reported already.
K figured it out.
If you Pass instead of Dealing, and the result of the round is such that the NPC dealer loses, the gold is removed from the sailor's debt regardless of whether or not it has hit 0, and the game immediately ends, but the sailor does not engage Aura and leave. Following this, you can talk to the sailor again, he will show negative debt, and you can play another round. This only works if you Pass. If you Deal, and clear his debt, the game ends properly and the sailor thanks you and leaves.
Btw, this is an amazing game. Totally GOTY for me as far as H-games go. I'd love to see more NG+ content. Title unlocks, perk unlocks, etc. Great stuff.
Hard mode is really difficult but it is doable, despite complaints.
Managed to get to 140/140 on day 67. Sure you have to save-scum a lot, but I will do that in any game regardless. (Though, honestly no idea how you could pull it off without the dice game glitch atm. Would take a LOT of skill, luck, and patience.)
Truly one of the top 5 games H-games I've played already.