While I'm normally anti-CA for buying properties because there typically isn't cash flow around here, I'm trying to convince my parents (who live in Redlands, just at the bottom of BB) to buy a mountain house up there so I can escape to it as much as I want and go snowboarding from there a bunch. :) The idea would be to vacation rental it out when we aren't using it ourselves, so interested to hear people's take on that aspect of it.

I'm not scared of tenants, but the latest tightening of anti-landlord rules is draconian, and I know from insider contacts that a number of landlords are going to be made an example of over the next 6-18 months.

Some of my thoughts:Majority of San Diegans believe in anti-growth yet cannot pass any anti growth bills. 

Out of town investors are amazed at how cheap these properties are, but they are also amazed at turnover costs vacancy and how anti-Landlord the cities are becoming.

Likewise, as Troy mentioned, on move-out.A moving fee is anti-tenant compared to a security deposit.  

In my understanding, when HOAs have bylaws that say 30 day minimum it is effectively their anti-AirBnB policy.

If you read my posts, I am in that "BP camp of anti-LLC" unless you really need it. 

BP can be a bit anti wholesalers at time so ignore that.

I'd get a healthy amount of liability insuranceMost insurers will tell you to remove any slides or diving boardsMake sure you have a proper fence so little ones can't get inThe pool drain must have property anti-suction devicesOperationally, I included pool maintenance / cleaning in the rent. 

(Even I had to move to a less expensive place to comfortably afford to buy) I am not anti tenant and do not blame tenants for being tenants.