Do you feel this is controllable or that it's mostly up to chance who succeeds and who fails? 

One of my biggest challenges and personal goals in 2025 is to let go of some of the control. 

Also make sure you understand everything about adding an ADU including value of the ADYPU, financing, impact from rent control, duration between initial expense and initial income, true cash flow (know the 50% rule, at 50% rent ratio initial property tax will be near 20% of income)- educate.  

I would also be concerned with land rent going up over time, and having no control over that.  

Bay Area, did a local renovation where I was able to do walk throughs with the contractor, and have pretty good control of this property, can check on it multiple times a week.

I liked craigslist because I feel in control using it and can tailor to my preferences.

Many of them struggle to relinquish control and delegate tasks to specialists who are better suited for those specific jobs.

If the answer to both added questions would be "yes", then you have a potential goldmine here.Combining the seller's concerns, and the reality of a big down payment being a negative to the seller (see Q: 1), you should be able to set the terms, with a lower DP, and controlled interest rate, to have this property CF and,...be able to sell the package to another REI down the road,...as long as you buy this using an LLC (a new one). 

Quote from @Gregory Wilson: This depends on what level of control you can exercise over the W-2 employer.

., constructive receipt doctrine, effective control over nominal 3rd party relationships, lack of genuine risk bearing and compliance with transactional terms, etc.).