Hard to get excited about $480 per month minus operating expenses (assuming I understood correctly)...unless of course you know you can expand as many of your expenses will stay flat while you revenue will clearly go up. 

Most "traditional" Chicago 2-4 flats are constructed with the units vertically.  

I would talk to your lender more about it but most just flat out won’t allow it and can call the loan due if you transfer after sale.

From a psychological standpoint, I think it's easier to take a little increase every year compared to staying flat for a long time and then a big jump to try to catch back up to market, even if you end up paying less overall with the second option. 

I'm guessing nothing .....I'd offer them a flat fee (1.5x rent) or tell them they will owe rent untill the unit is rented or the lease is up.

Or, google “flat fee mls” and there are plenty of sites now, which are in reality brokers, that will let you list your property for a flat fee.

When he wanted to go through the second sellers contract the same way I flat out refused. 

This year I've successfully flipped a house and purchased a currently fully tennanted 2 flat.

If past that date I'm not getting paid, so my vendors aren't and if it happens multiple times I switch vendors and part of that monthly mgmt % is for my time to manage this process and/or find better services for you. 2) Get agreement on flat fees for the various routine cost such as landscaping, inspections, lock changes, etc, and require them to submit their vendor invoices as backup.

The simplest way is to just write a flat fee for water / sewer into the lease as a line item.