I actively worked to pay down the mortgage so i could stop wasting money on PMI.

It's not a get rich quick scheme, it's a lot of active work and I would have 5 yrs in my head at a minimum before you truly become established and stabilized. 

How do I make this assessment?

If you have an active root...over time it will grow back in there unless you excavate, cut and remove. 

The city screwed up and liened Direct Charges on the common area which has an assessed value placeholder of $1. 

Calling the appraiser to see what you can do to push it up a "C-Level" would be smart before doing any reno also, might only need a few things to make it far more valuable in the eyes of the bank.I've heard of a tactic for figuring out demand, which is to put up a dummy or coming soon listing on facebook marketplace and see the amount of activity you get on it. 

Quote from @Henry Clark: Quote from @Greg Scott: I have invested in over 50 syndications, of which about 45 are still active.  

@Jon AveretteGreat to see that you’re from Tuscaloosa—I’m active in the area as well!

Do I give up access to transportation, restaurants, cultural activities, doctors, emergency medical care, religious and business activities, vet care and maybe more, to live in the country on my ranch or on the beach in a beautiful country, or do I keep access to all those things and live in the city? 

I have active leads with wholesalers and other agents, but quite frankly their deals are not good.