I have googled side gigs and nothing seems to be something I could do or really have the skillset for such as web designing or anything of that nature.

Of course, as a cover my a$$, I have to say that I have not evaluated your specific situation and this advice is just general in nature and you should consult with an attorney in your area.

 Short term rentals in Nashville Davidson county can only be held by a natural person, no LLC or any other entity   Also, owner occupied only.

In addition to the lessons you have already learned, a couple of mine:1) Natural curiosity - especially about "boring" things - can help you learn the vital information to move you forward2) If you don't know, ask someone, and/or do your own research.

I'm not pessimistic by nature, I've just been on the planet for over 50 years, and that's more than enough time to see what all can go wrong with best-laid plans.

One of our rentals has hot water heat powered by a natural gas furnace.

Oil & gas can only do so much

Given the historic preserve nature, I can foresee rehabbing these older homes with a ton of red tape associated with it.

Want asphalt drive way so you can resurface it with the dripping oil etc.

I do realize that a partnership and JV are different animals, but I didn't know which was more suited to this situation with the on-going nature rather than being a one-off.