I don't like one-time fees for software (he also says you can't buy it without signing up for his mentor/coaching program) because as a one-shot deal support, updates etc are usually pretty poor. 

An architect told me that even though ADUs should not be bigger than 50% of the main house, I should be able to permit this one with SB09 if I pay a fee (about $8k according to my agent).

Loan-related fees and expenses3. 

He pulled out a bunch of breakers, disabling the electricity.

As easy as this sounds, it's not simple and usually like pulling teeth.

Understand the fees involved and calculate the total cost for an entire year of management so you can compare the different managers.

I do like the idea of a check and when she pays closing costs ($515) for the title company and I'll pay attorney fees I'll have her write a check and get a copy of it. 

I will happily foot the bill for supplies so they aren't out any money out of pocket, but with the prevalence of contractor-stole-my-money stories, it makes it hard to fork over an upfront fee.

You could buy about 80 of them, but your cash flow would still end up at 16k which is about what you are making now (actual it would be zero once you account for property management fees). 

From a transactional cost standpoint alone, the fees on the way in and on the way out require significant appreciation to break even.