For example there are 2 forms of a lie; commission and omission.

I am an agent who specializes in commission rebates for my clients which really helps their investment numbers, so I find myself working with many investors like yourself. 

Pps  you do get to subtract the selling costs (in you example maybe $30k in commissions and closing costs) from your taxable profit.

If your broker markets the sale properly, you should be able to recover at least the excess in commission.

You can adjust prices on booking.com so that they are higher to make up for the larger commission fees. 

Save on selling costs by negotiating reduced commissions from RE agent.

You may want to threaten them with reporting them to their state real estate board/commission and state AG.

I wouldn't worry at all anywhere within 2 miles of downtown. you are in the very south of south side area commission but still very strong market. once you cross 104 it's different. 

But, with a negative cash flow and student loans around 7%, the math isn't working.We are considering selling the property (probably a private sale, so no real estate commissions) and paying off the student loans.

The seller is offering the buyer's broker a commission of 2.5% ($8250) and I am representing myself as a licensed real estate broker.