An Air BNB COULD be active and subject to SE- however it really needs to be fully operating like a hotel, offering much more in terms of services than what most offer.

Pretexting that I had to stay at the hotel to work, I met with independent real estate agents bankers and lawyers.

So far it's been in San Diego (at two different hotels) but I think next year may be in a different city

if you need to rent it for some of the 28 days are you in competition with the hotel for patrons? 

I considered SFH where I'd rent out all the rooms and keep one to myself, but this seems risky since I'll realistically be away for months at a time and couldn't manage the unit/other tenants.Then I came across some listings that appear to be hotel rooms for sale, with basically the facilities I need (a bed, toilet, kitchen), a price point I can handle (270-500k$, I'd do 20% down), and fairly high HOAs (~1500$/m?).

I own a short-term rental property that operates much like a hotel, so I carry large commercial insurance.

If she can't stay with friends or family for a few days, you are responsible for the hotel costs (or you can put her in a comparable vacant unit.

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 compare the supply of hotel rooms: Tulum only has around 10,000 hotel rooms while Playa del Carmen (Solidaridad) has approximately 45,000 hotel rooms, which is why big hotel chains are planning on opening in Tulum. 

There is a meetup on May 14th and then REI on Tap June 6th at the Crossroads Hotel!