If a mortgage has a deed restriction, not allowing short-term rentals that is not imposed by an hoa or a city government how hard is it to get it removed?

I’m naturally inclined toward this area because it’s within driving distance of major west Coast cities (L.A., San Diego, and others)—making it feel like a “natural” choice for a regional traveller wanting to get away for a short weekend. 

The City seems open to it as long as the contracts are structured the right way.

Or in other cities/markets?

One of the other factors that kept me from pulling the trigger is that the city has never passed any real STR regulation.

City-Data and Census.gov are solid resources, and sites like Rentometer can give you a good sense of rental prices.After that, I narrow it down to neighborhoods with strong fundamentals—good schools, low crime, and convenient amenities.

This way the lender is covered and only lending on the value that is legally zoned and compliant (in case the city took action against the non-conforming unit).

They are really changing the shape of the city and it may become incredibly expensive to buy out there soon due to lack of housing.

Hey @Nevin Wilkie. have you looked on the city or county's tax records to find the mailing address for the owner when it's different than the address of the property you want to buy?

It could even be (more) interesting from a lifestyle point of view as you'll get to stay in different cities/houses every time you go.