Due to a new quota system I have to enter a lottery to potentially keep these as STRs.   

But keep in mind:1) The application period under the new rules opens July 1, 2023, and it’s only open for a limited period.2) If two or more apply in one square block, and more than one application is complete and approvable, then the City will get out a bingo hopper and hold a lottery to determine who gets the one permit.  3) The lottery losers can apply for an exception in a process that involves input by neighbors and City approval, and the number of exceptions per square block is limited to 2.4) Operators who live onsite will be required for STRs in residential areas.

People are literally desperate for somewhere to stay while they wait (with a blank check in hand) to win the lottery by having a house come on the market that they can buy.

@Dave Foster  well to be fair a few of my investors have net worths that I humbly admit I will never get to unless I win the lottery...

We have lived in it for 5 years, and we just got our names pulled for the employee housing lottery offering us a much larger place to live in with extremely low rent.

As for the reply on San Diego being STR friendly it varies but San Diego city is not (on a quota and the best STR location hit quota that a lottery was necessary), but the county is most STR friendly.  

Additionally, a lottery system means renewal is not guaranteed.

We could hold a lottery of 3rd grade classrooms, to present there best proposal, and the winner get's to run the U.S. for a year, and we'd all enjoy the VAST improvement of things. 

It is possible to wholesale with no money out of pocket, but it's also possible to win the lottery.

She hit the lottery given the location and poor condition of the house.