Those companies you asked about are more for deal finding and direct contact to off-market sellers, is that what you are looking for? 

My insurance company sent guy to inspect once.

How does the transaction work between me personally and my holding company LLC?

It may sound nice to pay a 6% management fee but the extra fees can add up to be more than the other company that charges 10% with no additional fees.

It's by a company called Stonefeather Marketing and automates audience building on FB.

I own an HOA management company in Hoboken and it's led me down this thinking-path as well.

I will note though that lots of people manage multiple rentals without hiring a STR management company (myself included).

Currently my short-term management property is managed by the property management company.

When I filed a claim, my insurance company denied it because the property was under rehab and not rented.

Property LLC is owned by Holding LLCHolding LLC is owned by Jane Doe.If you were shutting down the LLC and wanted to just put the property in the name of Jane Doe who owns the holding company who owns the LLC.Do you actually need to transfer monies back and forth or would this be done by a journal entry as a non cash distribution?