They can continue living in their classic units for $X amount per month and you can agree to slowly raise it over time. 

You could find a lender that can go up to 80% LTV, thus even if there is this amount of closing costs, you still are ending up not bringing any money to the table, and essentially financing the fees. 

I feel like I need to have something to bring to table to also help mentor.

Chicago is off the table.

If it's your only offer on the table, then maybe you may want to consider listing your property to obtain more qualified offers.

However, with the market booming and prices high, I felt it was too risky to put all my chips on the table for a single property.

Who is contributing and covering what and translate to big $ at the closing table. 

Purchase price: $546,000 Cash invested: $49,000 Sale price: $595,000 Classic fix and flip.

Purchase price: $546,000 Cash invested: $49,000 Sale price: $595,000 Classic fix and flip.

You can also structure your offer with I know at least a 2% seller credit so that you can be paid at the closing table when you're buying.