Pros:
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he was upfront about his past
Cons:
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you’re uncomfortable with that past
Neutral/ Need More Info:
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the boarding situation
I’m the end, he can be the best guy in the world, but if this is going to bother you long term, y’all might just not be right for each other, no matter how ‘good’ he is.
As for the boarding situation: sex workers aren’t inherently bad. They’re people just like you and I, that need housing- It’s really the intent he had: was he just trying to provide housing to those less fortunate? Did he see the drug dealers, remember how much he hated doing that when he was younger and is trying to ease the burden in the hopes they can make a shift away from it? Or was it just a get rich quick scheme, and damn the consequences?
All and all, it’s less a question about his past and who he is, and more about if you’re willing to look past that- there’s also no right or wrong answer, here. Some people just aren’t compatible. It can be for a multitude of reasons, a lot of them just simple “we don’t mesh”.
But if he treats you well, and he’s living a life now that you’re comfortable with, then do some thinking on if you’re okay with that being his past. People screw up, they make bad decisions, they’re forced into situations they don’t agree with; it’s all about how they fix that situation long term. If he’s moved on, then you’re golden. If you have doubts that he hasn’t left all of that behind him, either do some more questioning or let him know you’re not comfortable intermingling your lives.