Lord knows I love a good pirate anything. This checks a lot of boxes for me. Some thoughts, in the order they occured to me:
I LOVE the addition of the personal quest for each character. Some of them could certainly use a little balancing, though. Patches' feels underpowered (unless it's useable multiple times? In which case it's good!) The Mists' also feels a bit underwhelming. Personally, I wouldn't voluntarily blow up my character for an extra 2d6 once.
The Flaws as an alternative to injuries is great. For simplicity I might even take it one step further and eliminate the Injury option entirely. As a player, I would take a Flaw every time over an Injury, just for the narrative addition even if it had no mechanical impact. Could always mitigate this with a mix of injuries & flaws so that not every level has a mechanical impact (but should still have some kind of description when marked to keep the narrative alive maybe?).
I keep reading "Captain BrokenHeart" as "Captain Beefheart". This is not a critique, but a reflection on me.
I, like everyone else, demand that you keep Kozel as an actual bear! Would love to see him finished, as well (personal quest, flaws.
I would also like to see all stats start with "B" for the sake of alliteration. Perhaps Omens could become Banditry or Buccaneer?
I like how you use Heat, but I feel like it would make more sense as a shared pool? Since narratively they're all generating Heat together on their job?
Pg 18, under "Player Roll", the first paragraph ends abruptly "or can be".
I love how you break up objectives. Lends to the heist feel in a way I was struggling to capture in my game. Very cool. I would like a little more direction on structure, as far as the minor and side objectives go. Sort of a flow chart of this objective can lead this that objective, that sort of thing.
I also thing this game would benefit from a ready-made list of Adversaries & stats, so the GM doesn't have to come up with that all on their own. Makes for a lot more prep work. I understand you didnt have time to playtest, but that would be something I'd heavily consider when you do, to help find that balance.