Sounds like you'd enjoy your quality of life if you own a piece of property near a nice park and within a decent commute to NYC.

Over nearly 3 decades, I have to say that the appreciation piece has contributed to my wealth at a much higher rate than cash flow.

The major 'repair' the PMC said needed doing did not actually exist, it was only a tiny repair.

It kills me to lose money after so many years of effort but I could at least have a down payment for perhaps two income producing rental homes that might actually appreciate one day (in a totally different state that is!).

Yes, it's harder to get into but 3 properties in CA will likely generate more true wealth aka appreciation than 10 properties in the middle of nowhere that cost 80k/piece. 

I think I created some confusion with the "as fast as possible" piece.

I actually earn far more than she does from my job.

That's where you'll find deals where the numbers actually work here in the Treasure Valley. 

This is so neither of us would have to pay capital gains on the sale since it actually stayed as a property for the LLC, my business partner was just bought out.

As you will notice that some of it was plagiarized by @Bill Hampton.He actually used to plagiarize the whole message.House hacking makes your tax situation more complex.You purchased a property that is treated as both an investment property and a personal residence.