That kind of restriction just doesn’t work for someone like me.I’m trying to figure out if I might be missing something in how I’m approaching this or if others have insights or examples of towns that not only allow STRs but also have laws that offer enough flexibility to operate in the way I’m aiming for.Many towns technically permit STRs but impose restrictive rules like membership requirements, ownership duration limits, or rental day caps, making operations challenging.

If you've already reached that end - ie if $4 million is enough principal to create residual income that you won't outlive - then I don't see any good reason to be buying out-of-town properties that then have to be managed properly to preserve your investment. 

I recommend that you engage with a real estate accountant to ensure you set everything up properly. 

:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

Recommend you look at Lockly locks with built-in camera, so you can also see who looked at the property and tell if the door was properly closed. 

However, to really do this properly and make it synergistic to the life style I want to live I need to bring it from 60-62% down to 30% by 2030.

You know, proper upkeep.Best regards, Stevan

Tenant quality and demand is generally good and usually there are no issues with proper screening, at least for those with decent properties.But for all of the naysayers on California, keep it up.

I definitely want to use the platform properly and not annoy others.

Quote from @Alvin Sylvain: This could be a good idea if executed properly.