You could still buy the property with your WY Holding LLC, but you may need to file a registration with the Secretary of the State of the state your are investing in to obtain financing.

Companies won’t agree to continue to lose money on their premiums.They have been denied here before - most major insurance providers (the State Farm’s, Allstate, etc) pulled out of the outer banks years ago.  

If the buyer and sell agree to the terms then a contract can be provided that can accommodate their wishes.

To provide clarity about my situation, I am currently job transitioning and would greatly appreciate insight on building a portfolio with income limitations.

Syndicators will provide references (albeit hand picked), and they can give you their experience.

We provide the residents with a list of names and phone numbers in advance, and warn the buyers NOT to arrive early OR stay past the end of the viewing.At the end of the viewing, our resident gets their e-gift certificate immediately by email or text.They are usually delighted and often ask us when they can host another!

They could have a lien on the property in case you default for some reason to provide the investor some assurances.

I can get you in contact with a agent who can provide an umbrella policy.

@Loren Clive I'd love any recommendations you can provide! 

The added challenge is that someone who wants to sell often doesn't want to be obligated to anything for another 3 years but also doesn't want their payout to diminish because clients (in this case property owners) move on to other service providers.