I am willing to help out in anyway needed in order to gain more experience and knowledge about real estate investing, wether it may be flipping houses, wholesaling, or buying and holding rental properties.

All investments have some level of risk, but multi family real estate seems like a better place for consistent gains right now than stocks or other investments (and I already have lots of exposure to equities through my TSP/401k). 

It is NOT our primary home, nor could we plausibly make a case that it is, so long term capital gains taxes would apply if we were to sell it.  

Again, I am not putting much money in my pocket each month, but I am setting aside $555/mo in CapX, maintenance, and vacancies as well as gaining appreciation in the home.

Welcome to the BP community.House Hacking is one of the most powerful strategies in RE for gaining property management experience, acquisition, etc. 

I thought that Brandon has used the Cash out Refi process to re-purpose the value gained on a property to purchase a new one.Can someone help me understand this, a better way to do the cash out refi, or should I call a different CPA?

I have a family member right now that will need to reinvest the $100k gained from a sale in NJ.

Maybe its gaining some winter weight?

There is quite a bit of capital gain on it (about 500K).

You’ll still owe capital gains on the other 70% and depreciation recapture. 3) start with the latest date of when the lease ends or you move in.