@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.

There are very successful people out there that most likely started in shoes similar to mine.