Half of all expenses come from mortgage and you should budget the same amount for repairs, maintenance, taxes, etc. 

As far as waiting for the market to slow,  your next purchase will only become more expensive overtime as home prices and interest rates rise.  

After college, I knew I wanted to pursue my law degree and I ended up back in CT because I missed my very large Italian family (also law school is f***ing expensive so financially it made a lot of sense).

He is looking to move in with his SigO but is concerned his rent wont cover mortgage/expenses.

How expensive is this multi?

Commercial leasing has terrific advantages - the sharing of EVERY expense.

While the end target result is primarily the same for landlords (maximize rent, reduce expenses, asset appreciation, providing safe & affordable housing, etc.), the PM's have either zealously or begrudgingly had to incorporate new mediums and technologies in order to survive and thrive in this industry.  

I know cash for keys is generally faster and less expensive. 

With Chicago minimum wage @ $12/hr, assuming 2 working adults (working minimum wage), household income would be almost 5x the monthly rent for my 2BR apartments, leaving about $3k/mo for other expenses.

As for the utilities and any other expenses, you would likely have to pay those out of pocket.