Tax Free Gains for Primary Residence (2 of 5 moving to 5 of 8)

[Stefanie K.]

Hi BP - Curious what others have done when faced with the deadline to sell under the current "2 of 5 year" rule and soon to be "5 of 8 year" rule in order to take gains tax free on a primary residence.

We own a very nice condo in Chicago in a very good neighborhood.  We bought at the bottom and the market has since gone a little crazy in Chicago and we now have a lot of equity should we choose to sell.  We use the condo for Airbnb (moved into a multi unit 1 year ago to make that our primary residence) and make solid cash flow on it.  We are mostly buy and hold investors and buy for cashflow.  

We do think there is extreme value in selling while we still meet the "5 of 8" criteria under the new proposed tax legislation.  Taking our gains tax free and then holding for another great opportunity to buy.  Anyone else thinking about this and what are some of the other factors impacting your decision?  I am leaning heavily towards selling and locking in those gains tax free...thoughts?