Another way to look at it also is if you have a rental and you can increase rent by $100 and sell it in a year for a certain value, are you better off selling it today at another value or holding it for another year and collecting income?

Due to age of owner's (70+), money to be made selling ( rapid increase in equity), change in the market area (over crowded beaches/Pigeon Forge strip) and life changes (divorces/death) the owner occupied/2nd home owners sold. 

Real estate has historically been a long term play.this idea that someone who otherwise never cared about real estate, can simply dial up a realtor and buy instant 4 digit monthly cashlfow is something born out of YouTube.

Selling to out of state investors.

Even then most homeowners are not motivated to sell. 

Or you can sell at a nice profit and reinvest closer to home.

I have been paying a lot of taxes every year from selling stocks and have a high W2.

Really, where I seem to use these most is with a client that has several million in stock market investments and wants access to funds without selling the stocks and paying the capital gains taxes.I probably wouldn't advise this...but you could look around for a custodian that has really cheap margin rates...and open an account there...and then take margin out of the account...That's what I do personally. 

Will he still have to pay capital gains if he sells?

If I was to return to Denver I wouldn’t look to live in this house.Should I rent for the next 2-3 and sell just before the 2 of the last 5 years rule?