@Sezuo Daudu like most investors on (and off) this website, and especially in Chicago...anything outside of “A” And “B to B Minus” areas just literally don’t exist to them.With $150k in funds you can almost two buildings if you play your cards right.

Owner occupied can generally be more selective on who they rent to, without violating fair housing.

It would be a vanity play, stoking our egos to move into a nicer house. 

Best guess if we were a plane flight away and not a fairly short drive, there would be less demand from groups of 15-25 or so people. 

If your portfolio is a good deal you won't have an issue finding buyers.If you truly have control of a package is one thing, if you are trying to play match maker with no real control, that is a weaker position.

Our game will have to play out where we are both onboard.

@Derek A GriffinInvesting an IRA into real estate is purely a diversification play. 

I play along when cold called by the refi call center guys, probably get my credit run once every 3 months while playing along.

Plus, how is a tenant going to view the fairness of paying half the water bill, when there's no way to prove they used half of the water. 

You have to be careful as a landlord to be in compliance with all current fair housing practices.