It's simple math of what compounding returns of such will be. 

I know that many things in the real estate world are hard to predict and out of the operators control.

You don't want to bring over poor operations to STR because you will also fail there.

LLC-A can do a consolidation exchange and purchase a tic% of the new property with all of it's sales.LLC-B can do a simple exchange from it's sale to a tic% of the new property.You can separate by address if you want. 

Great guy and excellent operator with great results.

Other syndiicators are not good operators. 

They may seem attractive on a spreadsheet if you are chasing cash flow, but the fundamentals are not as strong and these properties are  disproportionately impacted by capex and operating costs.

I will be managing all booking, renovation, and maintenance operations of the STR (besides mandatory front desk operations, and cleaning - required to be run by the Hotel).

My spouse and I didn’t learn our lesson here and took on a second partner in a real estate/restaurant operation and ended up again having to have legal action to sever the partnership when it failed.

Also, if I had no desire to at least take time to  see it, Id make life simple and invest in a CD or high yield fund.