From this CT information, it looks like it is an offset against your capital gains from other property, so you would have to find investors with significant capital gains and/or have them yourself. 

If you put enough down you can make it break even, but it just comes down to how much capital you have and how creative you want to get to make a deal work.

I believe you were right he would inherit your cost basis, so he would owe capital gains.

Excellent insight showing just how ridiculous this “don’t need capital, just drive for dollars” nonsense is. 

Honestly seems like a little overkill on this decision - unless its strictly a rate-term refinance because rates have dropped, it usually just should come down to a side by side comparison of status quo vs. refinanced (+ how any cash-out capital is deployed)

It was all risk capital on my part all up front since i would only get paid for success.. these were 200k duplex's at the time and I charged 30k EACH flat fee..

Where are you in the capital stack?

While it's exciting to cash in on a successful investment, the looming capital gains taxes can significantly cut into your profits.

Somebody should create a way for that money to be invested and benefit the renter whose capital/ sunken investment it is.

Often times, those are not deals with large capital demands.