I don't have any experience with the coaching program at Robert Kiyosaki, but I did go to the the free hotel intro where they upsold a class for $500.

I think of this as a commercial transaction, similar to a hotel where you have the real estate and operator/management.

If the property is not depreciable (IE the allocation of the purchase price to land), then it can escape ordinary treatment, but it also isn't depreciable.https://www.thetaxadviser.com/issues/2011/apr/casestudy-apr2...If you find  a cost seg provider that legitimately carves out 60% of the purchase price of a building to short life property, let me know who it is  My experience is more like 20-30% on average of the building basis from an architect based study unless it is something like a Hotel/Motel or Mobile Home / RV Park.

Talk to the people in the hotel.

You can diversify across markets and different asset classesSt Augustine is the capital of short term rentals Not enough hotels, the beach, the city, nights of lights.

If you sense any risk, just pay for a hotel for a few nights.....

I prefer a solid surface, tile or something similar like hotels do. 

Schedule E the piece the IRS put out about moving rental from Schedule E to Schedule C was because someone provided services above and beyond what would occur at a typical rental so they treated it like a hotel.

And even better you can stay so close to home for your first investments. 1.5 hours isn't bad, and if you need to make that drive for a day or even grab a cheap hotel for a night or two that's pretty nice.Best of luck.

The restaurant carries their own insurance policies, has licenses, and the property is insured under a commercial policy (which costs a lot more than a typical residential policy).Airbnb is run by individuals, most of whom don't know anything about running a hotel business.