I'm sure I'd invest nearly all of it, and nearly all the invested portion would be in real estate. 

You buy a portion of an individuals loan ($25 out of someone's $15,000 home improvement loan) and every month you get your portion of the payment received (***there is risk involved!

Think about what that means and the effect it has on your payments while holding the property for flip, or renting it out for a few years...My initial loan payments consisted of the PRINCIPAL portion of the loan only...  

At best, the room mate might have to cough up a portion of the rent for the time this guy occupied the other's room, but that would be up to them to handle it.Good luck,  I rent to college kids too and it is always entertaining!

I have never been asked to actually wire the money into escrow when giving my signed portion.  

My take on Chicagoland is despite the possibility of property tax hikes you still have outstanding cash flow possibilities throughout a very large portion of the real estate and rental market there.

It's in the upper right portion of the sheet in green boxes.

Also - maybe you could offer to do rentals of no less than 1 week to avoid turning it over every few days.Secondly, wondering if you could structure some sort of rent to own situation where the monthly rent is increased and a portion of that goes to the buyers  downpayment (maybe an extra $200/month so rent it out for $1,400) if they end up purchasing it within a certain period of time.  

Some markets are more desirable (say where you can rent a home for 700 and the lot rent portion is 300, and you have a good spread).  

My question is, do I need to set aside a portion of the profit for income tax?