Depends on the lender.If it has yet to go to foreclosure and you are trying to buy it prior or at sale - the answer is a hard no. 

Then you can do a 1031 exchange or sell it at a lower tax rate. 

I think he is a great guy and isn't his first rodeo with investor funds.We can do some legal checks if you want that type of search, lawsuits, prior names, etc.

The mortgage has gotten out of hand due to property tax increases, miscalculated escrow, and an increase in my interest rate from an initial buy down, increasing from $2600/mo to $3200/mo.

Definitely make those assessments during inspection or prior to making an offer if you can to save yourself the time. 

The “Big deals” are…You have to buy something you don’t already own, not pay off debt, renovate a home you own, or build on land you already own.You have to spend all the “cash” you receive.You have spend more than your net selling price.You can never receive or have control of the cash, you need a QI PRIOR to selling. 

Do that every 2+ years, sell tax free, repeat, and you can be set for life ("live in flips"). 

@Andy LanyiGood comments on how to reduce tax bill. 

Refinancing  immediately prior to a sale - yes that is a cause for some seasoning. 

According to the City of Chicago tax code, it costs $5.25 per $500 of the transfer price.