I currently have a rental that used to be a primary residence.

I purchase my 2nd primary residence and there was about 4yrs of back dues, granted they were only a fraction of what you are dealing with but they just forgave the balance on mine.

They are considering selling the home and when they started researching capital gains, realized that they would indeed paying them as the home has been a rental longer than it was a primary residence.

@Alexander FeliceSFR, especially if it is your primary residence are difficult decisions, and thus what I call emotional decisions.

I just don't want someone coming after my personal residence if the bottom falls out of the market.

Suggest you find someone who can set up a trust for probate etc and they can recommend which state for where your LLC should reside.

Is this a flip, a buy/hold, or intended to be your residence?

Should we cash out refinance out primary residence to pull more cash out or should we just use own cash reserve+ HELOC for next down payment and any extra fees?

My question is the following, if I buy an investment property (while continuing to rent where I live), does that prevent me from qualifying for an FHA loan later on when looking to own my primary residence?

Even when house hunting for my residence a house would be gone within days of being listed.