Hey @Regina Bailey - If for some reason you didn't get the Chicago lease from others above feel free to reach out to me and I can provide it.

The latter seems to provide a middle ground that could enable professional maintenance oversight while allowing me to retain some control, mainly through tenant communication and management portals like RentRedi.

Based on the information provided, it seems like this could be a solid long-term investment opportunity.

The deposit was provided and he actually ended up paying a year up front. 3.

Open escrow with homeowner, end-buyer, and self; self transfers contract to purchase to end-buyer in Title/Escrow, and provides T/E with end-buyer's contract with self: agreement to purchase, and fee instructions for self ($10k + difference if any) to be paid out of closing escrow5.

For how long are that service provided?

I work on a local team that provides free educational classes on investing and I am happy to help you with any local connections I have that may be helpful to you in your journey! 

Transferring to a LLC provides you fake protection (note I am not an attorney but have common sense).

Evictions with any tenant are much easier for non payment of rent because it is easy to provide the proof. 

Best to seek counsel from your attorney and tax professional but if you are going to insist on saving a few dollars, best to provide more specifics on the type of partnership you are contemplating so you can get your hands on something that's remotely relevant.