Real estate's "gross rent multiplier" is Wall Street's "sales to revenue",  "cap rate" is roughly "P/E ratio".When evaluating markets and investments I tend to start with GRM (or lazily the 1% rule), then attempt to return a cap rate based on assumptions about costs, then I work my way to multiple years of projections (assumptions about inflation, amortization, tax benefits, etc), and if I am partnering with one of my smart friends I have to pull up an IRR (internal rate of return).I also look at regional employment levels, median income to rent ratio in the zip code etc. 

Plus factoring in the 5k or whatever number that is you are paying for "coaching" it just seems like you have to be in this thing for a long *** time to make significant money WHILE assuming a much higher level of risk. 

A mentor can accelerate your growth, no matter what level you're currently at.

I think I'm just not understanding what sort of realtor would be willing to help do something like this because I assume most realtors are used to finding you a move-in ready primary home and that's really what they know, and that the price needs to be a certain level to get a worthwhile commission.

Since your metric is modest cash flow with long-term appreciation, focus on neighborhoods with a history of steady growth and tenant stability.As a realtor, you already have the skills to analyze deals—so trust your instincts and take action!

It seems like there was a lot of hype at the government level but owner/occupied demand hasn't been what they thought it would be.

The software doesn't provide that level of granular detail that can mean the difference between 2k and 3k a month. 

As for strategies, do you have any other skill set that you can bring to an experienced operator?

PM is a great foundational skill to move you forward.

I maintain even break even on valuation (which is rare in SF Zoned areas), the ADU has big disadvantages versus new property acquisition including financing, level of effort, rent control, prop tax being based on cost rather than value added, length of time including length of time from first expenditures to first income, reduction of something from existing unit (in your case existing home lost its garage).Did you see starting next year Mf can add an ADU per unit up to 8 units without any affordable housing concessions?