Jim's father a pirate?

Could Jim's father have himself been a former pirate or know something about these pirates beyond what he lets on?

It occurs to me that it may be more than coincidence that Jim's father seems to suffer a terminal decline in health as soon as Bones arrives--in much the same way as Bones declines once Black Dog and Pew appear. The similarities are fairly striking. The stated reason for Jim's father's decline--the stress of Bones not paying for his room--don't fully make sense to me. I assume as a businessman Jim's father has dealt with deadbeat guests before and knows how to handle the situation. Plus Bones isn't a deadbeat: he offers to settle up his room as soon as they let him know, and he always pays Jim his wage. It seems to me that there must be something more to the relationship between Bones and the father that we aren't told.

Plus Jim immediately seems drawn to Silver as a surrogate father figure. Isn't Silver--initially--living a life much like Jim's parents? Silver runs a bar by the sea with his wife--a very similar life to what Jim's parents have.

No actually, I don't think Jim's father had a mysterious past as a former pirate. I think you just take things at face value, they're honest innkeepers who have some shady characters as patrons. In fact it's Jim's mother who plays a pivotal role in the beginning, by having Jim rifle through Bones' belongings. Jim is sort of a 'feather-in-the-wind' character, he has luck on his side and it is that luck that sees him past the adventure.