The first one baffled Neon -- the game wouldn't give him new clothes. This wasn't the end of the world, he was content with the ones given at the beginning.
Second, he wasn't getting noteworthy gold from the loot drops. As he neared level 10 Notoriety he didn't have enough gold to buy the Romp family favorite chest tattoo.
A typical Romp family pirate goes with his brothers to Kingshead and levels sword on the six vets--that is his speed ramp to level 10 and there is quite a bit of gold given. Also, in a family with half a dozen pirates hovering near 200,000 in gold it isn't hard to get a pirate to give you gold playing poker.
For a third surprise, the "side" enemies at Dark Hart were particularly mean. They didn't just randomly find him and kill him--the one Dark Hart's right side was giving Neon an evil eye and attuning and killing him as soon as he spawned.
To counter this Neon parked at the doorway to the gun shop ready to jump in to break off the attack. You can rest assured when Neon gets the strength to attack those side monster's he's going to kill them viciously. And that will be soon...
Dark Hart did give Neon good gold, thus solving the "currency shortage" problem.