I'd sell #1, even if you have to take a loss on your equity.The market does go up over time, but most markets seem to be stagnant right now, so when does that change?   

Additionally, please share if this was a scam or not.

And then you got the vacation rental market.

Additionally, I know the Waivo product for STR covers intentional and accidental damages.

However I believe it’s great to have two independent sets of eyes (in addition to your own) on the books to make sure everything is accounted for and running smoothly.

While a properly maintained TN LLC might be sufficient for those who diligently follow corporate formalities, the additional layer provided by the Wyoming entity can offer significant extra protection, albeit with increased complexity and cost.

Low or no down, seller financing and low or no interest with a balloon payment later is the holy grail (location, building condition, market also matter but it sounds like you have all that).

My local market is cost prohibitive to invest in and the thought of assembling a "team" of unknowns in another market was scary. 

In addition to your down payment, plan for closing costs (around 2-5% of the purchase price) and set aside at least 3-6 months of expenses for repairs, maintenance, and vacancies.

Hey @Christian Artuso 👋🏽I’m RE agent + investor in the Chicago and Northwest Indiana markets.