NW Chicago is very expensive as a rental.

That is very standard.

The brokerage doesn't matter as much unless you are selling off market and they can share within their office.

There is a saying "if you've been sitting at the poker table for more than 15 minutes and you don't know who the patsy is...then you're the patsy".

If your 5th deal is good, you should be able to find funding outside the banking industry.

The “buyer beware” philosophy is fine for commercial transactions, but taking “advantage” of home owners when they’re most vulnerable and lack market sophistication is something no right thinking person wants.  

(saving the money to have your own deal is the worst idea)

To some on here that is not much money but you measure it in relation to your income, my guess is it is a big % of your income. 

100% occupancy for a LTR is normal.

Money is money.