Also most people employed, so even if it is a struggle they can still pay the bills.

Deed holder is almost always named because its the easiest party to find...deed's are recorded and public.It also sounds like the Wyoming LLC is the deed holder and the transactional costs associated with re-titling the real estate is likely going to be more expensive than continuing to maintain the Wyoming LLC.

I changed my strategy from 2 years ago of acquiring more doors and "cash flow" to now looking at the asset if I continue to buy. 

The departing tenant says she will continue paying rent, but I wouldn't bet on it.

We have had hosts on the platform since then that are continuing to do well and add units.

If this concept is unfamiliar, then continue to ignore it.In closing: The dangers of shifting the timing of your income, expenses, and business transactions.A purely mathematical exercise may indicate some beneficial timing for this or that.

I also purchased a multi-parcel farm property in TN where the trust who owned the property was out of money and needed cash to continue. 

This could create a disdain for flipping properties and not continuing on the path..The other option could be wholesaling it to start a path to build a war chest to go out and do the first flip with your own money down. 

I will continue the journey in this thread!  

Even with multiple units, with current interest rates and a competitive market (prices have continued to rise even with higher interest rates) think the Madison market is a stronger long term ownership strategy, where the bulk of your return will come when you sell from appreciation in rents and property value.