Its going to be managed by a property manager and thus a passive investment which is allowed per h1b rules.However, I am being needed to procure state and county hotel tax certificates which almost seems like I am launching a hotel business in the records of state.I am starting to wonder if this can cause issues down the lane when renewing my visa or applying for green card.If anyone else has a similar experience or own STRs on h1b, urgently want to discuss this with you.

If you've already done that or have a smaller budget like sub $30MM, I go to the best neighborhoods in the best cities, and buy the most distressed houses.I flip the one's in states where it's hard to manage tenants or re-fi into STR, re-fi out with 1-1.2 DSCR in areas where managing them is convenient in landlord friendly states.

So, that’s a plus that I’m not a complete stranger but none the less still a stranger (I’ve never met the owner but met his property manager when I was home for Christmas last year)  

Some real estate investments grow a little slower and even though there is monthly rents collected, there is deferred maintenance costs and management requirements depending on what type of properties.

If your personal finances are a mess, then you're going to have trouble investing in real estate, and you probably should NOT use leverage to buy real estate.

The owner owns it free and clear and it's managed by a local property manager.

This would include your agent, property manager,  and contractor.   

The full guidelines on the Freddie site for LLC are:Permitted Transfers of Ownership subject to conditionsIn situations where all of the following conditions are met, Freddie Mac will permit a Transfer of Ownership of the Mortgaged Premises:-At least 12 months have passed since the Origination Date-The Servicer has complied with all mortgage insurance requirements applicable to the transfer-The transfer is to a limited liability company (LLC) or limited partnership (LP), provided that:The managing member/general partner of the LLC/LP is the original Borrower.

Property Management and Found it.

Before making any decisions, review the information provided by San Francisco's Office of Short-Term Rentals website, consult with local experts such as real estate agents or property management companies that specialize in STR.