Someone getting into REI using the STR to create a positive cashflow can only expect (2) as a natural result, not only from the community taking action against businesses operating in residential neighborhoods, but also economic reversals where the travel industry takes a hit.BTW: Tourism has been with us since the automobile and communities thrived a long time before the advent  of STRs.The NIMBY principle is heavily at work on this subject and historically, has been effective and successful in managing change.  

You would have to seek alternative financing for the 2nd property.  

Unfortunately, the nature of student loans today makes them more analogous to having a mortgage than the quasi-car loan (in rate, term, and principal amount) we were able to walk away with 20 years ago.

A chalk board that people can sign for no reason would also be cool..obviously these are just bandaids.. but unless you want to remodel, drop prices etc, its not a bad alternative.

You'll always have the wannabees down at the REIA & Chamber bragging about their "awesome" returns on a beach rental, but the best are usually low-key and are true real estate professionals.My overall opinion on this: You'll never be able to gauge your returns against others due to the nature of real-estate.

Buy and Hold properties that are kept for 10, 20, 30 years will naturally sees up and downs in the market, but I feel that during tougher times more people will be leaning toward renting anyways, making the buy and holds - if purchased for the right price and in the right market - still a cash flowing opportunity.

It either happens naturally over time or ... take a deep breath ... it doesn't.  

In practice, it's really not so much different from mezzanine debt.The preferred equity strategy is a great alternative to debt financing in cases like yours where you already own the property and don't really want to go through the process of refinancing.  

We are contributing a rather large sum to the buyer's closing (10k), and would naturally want to see how much of this sum will not be used by the buyer.

They are currently leaving the area in droves.For many Bay Area residents, Sacramento offers affordability and enough of a "big city feel" to make it an attractive alternative to the Bay Area.