He's indoors most of the time now, and when he does go outside he stays in the yard 90% of the time.
So there's a 10% chance every time he's loose that he'll run off. That's a risk that in my opinion, shouldn't be taken. I do not appreciate dogs off leash coming and bothering me or my dogs, it doesn't matter if I'm in the country or the city. While there are some dogs and some situations where off-leash is OK, most of time it is not, especially if you are bothering others.

No I don't think how he acted is ok, nor do I think whatever illegal activities he's doing is ok. But if you want to keep Max safe, don't let him loose.