My family has been operating real estate in San Diego as a primary income business for 3 generations and it seems odd that a real estate business would have to only operate as many STRs as they have employees who could apply for the license.

If you do #1, I'm willing to bet your expenses on the property your first year are higher than your rent now.

Estimate time (in this case you know 1 guy / 2 weeks, sounds about right with odds and ends)80 hours times $30 is 2400 in handyman labor, that's 4,800 a month including truck, tools and taxes - income is so low, he would not qualify as a tenant for us

In fact, if someone asked me today who the best bet would be, I would say Nimius--and this is based on the many calls I get from out of state 'investors' who have bought properties in the hood, typically at way too high of a price, and want to sell shortly after and who those companies/people are that sold them or are managing these properties.  

I find this kind of odd, especially if I provide written consent.

Like previously stated, the big box stores are probably your best bet w this situation, or a going out of season sale.

And I bet none of these so called experts can reproduce our results.

Bet your cards on living for very cheap or near free AND appreciation here in California.

Send him a copy of your application and odds are you'll never hear from him again.  

That's going to be a tough sell.Well, If you're serious about this then your best bet is probably to find a successful investor actually doing what you want to do (*important*).