Get as many units as you can with an FHA loan and don't buy a value add.

Now he is 21 years old with a big dream of being one of the best versions of himself.

How should I proceed with structuring this plan?

@Najeh Davenport  Start with the local zoning office. 

But like he said, f something goes wrong with ANY of the properties you have debt on, you might be in a pickle.

That seems to be different with a DCSR loan?

Obviously, the rules will differ from state to state.The most successful buyers have trusted bidders with cashier’s checks in multiple denominations (for cash sales) and the actual buyers have field runners and people to monitor multiple prospective properties at a given time and check sales status for postponements due to BK, etc.This is the case in larger metro markets where many properties could go to sale but few do so.There are often better ways to acquire properties then auctions.

The house is worth 275,000-290,000He owes 162,000 I want to take over that loan with a 1100 mortgage payment and the tenant pay 1900 per month.

I've flipped several properties in Eastwood Hills East and surrounding neighborhoods, with about half selling to homeowner occupants and the other half sold to investors with tenants already in place.That said, the specific property you're considering is key.

What you want to discourage is the tenant 'helping' you with feedback/action that is outside the scope of the lease.