Fast forward 2 years his landlord mentioned in passing he might sell the property; I was the first person on his mind.

You now don't seem like the type of person most of us would accept a recommendation from.

We are now at 21 doors under management and 3 are personal units that we self manage.

This is our boilerplate language:Insurance: Tenant should obtain a renters’ policy of insurance on their personal property.

But I don't know your personal situation and all the financial details. 

Also, long term, I expect Sac will enact tougher restrictions on STR, given the intense housing crunch we're experience, so I personally don't expect that to a be a good long term strategy.

CA has more than half of the nations homeless/unsheltered persons. 

Personal guarantees are EXTREMELY common.

I want to exit as I don't get any personal use from the STR being 20 mins from home and would rather apply the capital to another opportunity in multifamily (LTR) or another STR in Hawaii where my brother is a broker and now manages STRs.

If you have a chunk of money to get going I'd personally buy the biggest thing you can if you don't I think house hacking into a 4 plex is great.