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

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.

I’ve seen situations like this before..one old friend of mine in Austin had a few industrial buildings where the cash flow was decent but not dazzling, and he was itching for a way to ramp things up.

Think of it as the rough sketch that helps you figure out where you want to swim: Omaha’s stable single-family rentals with decent cash flow and strong appreciation potential, the sizzling up-and-coming pockets around San Antonio where off-market deals still lurk if you’re willing to roll up your sleeves, or those tight-knit Chicago neighborhoods where a trusted investor-friendly agent can point you to contractors who won’t ghost you mid-reno.

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).

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?

If the houses are in decent shape and could get traditional financing do not sell seller finance.