Not only should you have your attorney handle this, but also have your attorney provide a new lease with as many landlord protections as you can get under Chicago & Illinois law. 

But clearly they are not experienced enough to be handling this on your own. 

I ended up building a team internally to handle the management and make it more of a passive investment for me.

Have you had experience with this in the past, and how have you handled it?

I have some good connections with attorneys and title companies that can handle everything you are talking about. 

Also a side note, for all the locks I have swapped I have put in non-locking handles to try and further reduce the likelihood of a lockout.

Hi @John D PollardThere are two companies I use.American IRA will set up a self-directed 401K with checkbook control.Quest and American IRA will both set up and handle administered 401ks.If you are strictly lending I would use American IRA with checkbook control.Our buyers pay 12% and 3.75 points to their lenders or 20% of the net profits whichever is greater.If your going to flip homes then the Aministered is the better option.

In some states (including Texas, where I am), the term “security deposit” has a specific legal meaning and certain rules for handling.

Since he is very unfamiliar with this process and this would by my first seller finance, the house is on the public market so he is contracted with a listing agent. he is curious how the commission for said agent is handled. 

Should I expect my PM to handle taking over the service of the electric and water bills and charging that back to me?