I’m going to disagree with @Chris Seveney and say whether an assignee could force a sale directly would be a state law issue and heavily dependent upon the contract terms. 

You can opt to automate rental payment collection so Turbo Tenant collects rent, and deposits it into your bank account. 

In this option your agent would either get paid from you directly in your closing costs OR from the seller via seller concessions.like Russell said, if you are comfortable with the transaction and understand what you are signing and you don't need things explained and you have connections with inspections and title companies then go for it.

Best thing on looking for info on a cost segregation study is to go directly to a firm that specializes in it.

It markets our properties, screens our tenants, collects our rent, deposits it into our bank accounts, has full accounting and reporting features, has a tenant facing web portal & app where tenants can log in and report maintenance issues and see their account, etc, for $2/door/month - but they have a $45 minimum monthly fee... so up until you cross 22 doors it would be $45.

That’s the kind of agent you want in your corner, especially in a competitive market like San Antonio.While I haven’t worked with him directly, I’ve spoken with an investor friend who did.

What do you do to ensure that the tenant is responsible for security deposit disputes since that is the largest reason for owner lawsuitsHow familiar are you with the newly changed laws that can affect you the owner if they are not used correctly?

For the water metering- are you doing a sub meter like PUBS or are you putting in direct meters for every home?

-When a tenant moved out, the management company refunded their security deposit but failed to account for damage, such as holes in walls and outlets ripped off the walls, leaving me with repair bills and also tenants moving in without the repairs being done.Stuff like this that is consistent and when I ask questions they are defensive, when I ask for more quotes for high ticket items they are defensive. 

Seller financing can be a fantastic way to get into a 4+ unit property, especially in a competitive market like Chicago.Have you started reaching out to owners directly or networking with agents who specialize in multifamily properties?