@Unknown-username-123,
I do not care about you guys age. I mean for you maybe but not for him.
Prison ? Why ?
Honest to gosh it sounds silly that your a young person with somebody from jail.
The reality is that you do taxes, and you want to include expenses like your mortgage, travel-expenses ( gas, public trans ),
I mean wow I am impressed with the mortgage rate, I wish I had that, all I am hearing about is taxes for the property being a problem. That sounds amazing.
If it was me, I would ask my spouse, "where are you going in life". "What is your goals" "Who are you" "What are you good at that others are not". Takes those into consideration.
If he could go back to school to be a medical doctor/ physicians, I would do that. Otherwise I would look for various training, in which he could study, and practice and would be happy with, that allows him to work. If he has an y dispositions that might be a problem.
What does he do for work right now?
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Does he have any kids?
beyond that in my opinion I feel your wasting your time, and you and him should just get married, and have kids already. That is where this stuff is going down the line, and it is a waste of time to question "Should I charge rent?"
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If you was my sister I would say "Jail" what for? It is was $#$#@$k up then no.
I would rather go to a college and look for a some guy that actually wants to study something. I do not care if they were 40.
Their is so many directions this could go...... Again he should study, get a certification, bachelors, masters, etc do something with his head. Take a city exam for all I care.
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Make him go into a training program, something But again "Why was he in jail.