1. Regulations are in the works. The next meeting is scheduled for 12/12/17. These regulations propose limiting non owner occupied rentals as well as other items. The legality of short term rentals, although taxed, is even up in the air. This is very contentious in many communities.
2. If you currently rent your property on a short term basis in the city limits, you must register and pay transient occupancy tax as of this writing for most AirBnB/Vacation Rentals the amount is 10.5%. This fee is traditionally passed on to the guest.
3. Know the CC&Rs (rules) of your homeowner’s association before you buy or consider turning your property into an AirBnB. Many associations regulate the minimum length of rentals allowed.
4. Ask yourself, can I truly afford this property if my ability to rent on a short term basis is impinged upon or taken away altogether? Run the numbers as a long term rental.
5. Most owners are overly optimistic because of the stories of people renting rooms for a weekend in their homes and paying the mortgage. If you purchase a property for this purpose, remember this is a business and with businesses, come costs. Who will manage the property? Clean it? What about linens, furnishing, and the like? The logistics of short term rentals are far more complex than the popular press make them.
Many of the cities outside of San Diego have their own vacation rental regulations as well. This is a very specialized area and not nearly as simple as most make it out.
I owned my own vacation rentals, and operated a vacation rental management brokerage, so please call on my expertise when considering this type of investment in real estate.