While my investments are up this year, I will use tax loss harvesting strategies to help offset the hit from the sale on my investment property this year.I will still invest some of the proceeds of the sale in properties as the opportunity arises, but now I am able to reset my basis and not worry about the large cap gains hit or continuing to put that large of a nut into continual 1031 exchanges if I decide to sell in the future.  

Additionally, I’m up for long distance investments but I would definitely need some mentoring there because it was hard enough managing the VT reno from Boston.My current strategy would be to rehab/flip a few houses a year so I can leave my W2 job and also add some buy and hold rentals (MFH, STR).

I’m active duty Air Force with a year left before retirement.Another great strategy is using your VA loan to purchase a multifamily property.

What innovative strategies are real estate professionals using to minimize capital gains tax on property sales?

Exploring the idea and it seems like it could be a good strategy. 

I am pretty sure that whoever wins the auction at say 500k, will have to pay the Property tax liens owed on top of the 500, that it's not already baked into the reserve price. 

I am looking at the same strategy.

And if so would I be able to do a Cashout refinance like people do with the BRRRR Strategy? 

Hi Connor, Congrats, househacking is a great strategy and it sounds like you have a good plan in place.

You might have some luck with a house like that in midterm rentals but you'd have to be willing to really work on your strategy.