I think Blacksmithing is bugged, I got it maxed out and it says 50% chance on to fail and it stay the same, but instead it for from +4 etc; etc; to 0. Big money sink.
Level 25 rogue, I've found the best strategy for making money is spamming Deadmines. With 5 inventory spots, in a very short amount of time I can loot 5 blues and make a good 6 and ahalf gold or so. Spam that long enough and it's okay money.
I have a Vanguard with 4 other crew members. And I'm almost the guildmaster for the buccaneers. I've never once needed to heal in this game. That's a part of the gameplay. You heal when you get to a town. That's the only healing you get
I've been playing this game for almost a week, an hour or two every day when I have spare time, and I'm still not done...it really is a game that never ends =P