He also lived in Property A for ~2 years within the last 5 years (though he's been told by his CPA that he likely won't be able to avoid *any* capital gains because of the way his previous returns were filed.

Well done on the historic gains though...

and personally I have yet to experiance a down side that would outweigh what I've gained... so for the fun of it, to those who have house hacked and do have something to share when they thought "I'm crazy", "I can't believe I did this" please share!

I would then consider selling it after a couple years to get the capital gains exemption if there was some good appreciation.

But after I had a few rentals under my belt I refinanced them, pulled the cash out (not subject to capital gains tax) and paid those loans off.

@Jonathan Stone I got you brother, whenever I went into the city code and ordinances page to look it up I need to have certain things built and in place along with an application to gain an operating license.

Plus you can be gaining equity.

So, here I am, ready to learn, and eager to gain the knowledge I lack.

So, here I am, ready to learn, and eager to gain the knowledge I lack.

If I do a complete BRRRR, and retain equity after the refi, then decide to sell before the 1 year mark, will I be subject to short term capital gains tax?