I don't really care if one party moves out, but that doesn't mean they don't have to perform. 

It's more of a luxury property but supposedly they can perform really well as full time rentals.

Also, if I am ever sued in court and during the discovery process I'm asked to list all my assets, I can't just not casually mentioned the Wyoming LLCs and trust right?

Is this consistent with what I should expect to pay for the returns I had performed?

Owners mistakenly ASSUME all PMCs offer the exact SAME SERVICES and PERFORM those services EXACTLY THE SAME WAY, so price is the only differentiator – so, they often select the first PMC they call or that calls them back!

Also, if I am ever sued in court and during the discovery process I'm asked to list all my assets, I can't just not casually mentioned the Wyoming LLCs and trust right?

It might be best to run numbers on existing and see if by goin with a new build can perform better.

Your point about long-term mindset really resonates with me; it’s crucial to consider how a property will perform over the years rather than just the initial cost.

Under the IRS rules, a person  qualifies as a real estate professional if: (1) more than one-half of the personal services the taxpayer performs in trades or businesses during the tax year are in real property trades or businesses in which the taxpayer materially participates, AND.....(2) hours spent providing personal services in real property trades or businesses in which the taxpayer materially participates total more than 750 during the tax year.Like @Greg Scott and @Russell Brazil mentioned above, I don't believe that you would qualify as a REPS, but if you are going to try it, make sure you document it very well (i.e. with some kind of proof, like time cards, mileage forms, and/or receipts, etc.) so that just in case you do get audited, you at least have something to provide to the IRS agent. 

At the end of the day, everyones ultimate goal is to become the bank and simply lend out a pile of money and collect a return rather than having to do the grunt work of making these assets perform.