An SFR can be 100% vacant versus one vacancy in a triplex is 33.3% vacant.

You can then measure the cash flow impact versus the potential cash you would obtain upon a sale.

(And then any state implications)Given this isn't pennies we're talking about- working with a qualified professional to help mitigate the tax would be your best bet. 

JD, don’t disagree on some of the points you’re making above on responsive Web versus mobile app development, but it all comes down to level of engagement and what you’re looking to do with a site or service.

Kind of like asking if people like cars pro/con; then finding out later you're a car salesperson; versus Truck/Motorcyle/Mass transit.Read back through my comment and yours, we said the same thing. 

We sold 3 locations that had little debt on them with great cashflow, stayed heavy in cash, our stock return was only around 11% versus 25% since we went conservative, have two projects banks have already greenlighted with no downpayment on our part using cross collateralization with other properties- built in $2.5mm equity creation in 3 years in those projects, on hold for now.  .   

It's stopping me from scaling to a much larger portfolio leveraged versus a smaller paid off portfolio.  

I appreciate the reminder as well that if the gain is fairly low then it may make more sense to just pay the capital gains taxes now versus 1031 exchange. 

If only tax expertise is what you need, an EA or a CPA with a tax specialty is your best bet. 

Do you want your son to bet the financial outcome of his 20s on this seller's ability to make good choices?