I'm fairly confident that we made the websites baby proof for the exact reason so every investor can easily understand EVERYTHING that we do...

Selling the property offers a significant cash sum, enabling you to potentially diversify your STR portfolio by purchasing multiple properties outright, fostering a more passive income stream.

Maybe you can sell/merge the two existing companies into one first and then perform 1031 exchange.Let's have the 1031 expert respond @Dave Foster

Even though I didn't see it first hand(thank goodness for facetime), I had some trusted boots on the ground that allowed me to feel confident that they understood my requirements and had my best interests in mind. 

I'm confident in my value as a broker considering the risks of purchasing the 'wrong' property being catastrophic.

Is there no viable venue that private money lenders can meet directly with borrowers, where both have goals that can be met in truth and with confidence?  

As in my case, working as a full service Property Manager, I'd imagine that would instill more confidence that a building will be taken care of, units will be leased, preventative maintenance will be done, etc.

@Dave Foster Thanks for this!

Obtaining competent management was an issue, I have no confidence in the service personal in the local area.  

If you are not confident the area will appreciate (value and/or rents) or grow in demand within your time frame, then you may want to think about a plan of how to best dispose of that liability.