@Tyler MilesIn my opinion, the best thing to do is to put yourself in the shoes of a renter.

@Daniel Botvynko If I were in your shoes, (and I was in a similar situation years ago so I can draw on personal experience), I would go work for a year with your brother.  

If I was in your shoes, I would definitely house hack and use as little money down as possible.

If it were me in your shoes, here is how I would proceed: 1.

If I were in your shoes, I'd have your agent pull rental comps for you.

If I were in your shoes it would be the numbers that tell what I should do.

E.g if I'm buying a pair of shoes for $120 today, it means that I'm basically spending $10 each month this year to own this pair of shoes.

I have been in your shoes and it’s a hard uphill road.

If I was in your shoes and had time to kill but money sitting there I would invest it in index funds so it grew until I was ready to pull it out to invest in real estate. 

If they come off aggressive or not well intentioned/motivated when you address the issue, then drop the facts on them (eviction on record/no place to live/court) if they are positive and motivated then work with them and put your hard working self in their shoes and show empathy.