And when I speak with people (or write on my blog) I'm always VERY transparent about the unique challenges of the market there.

It would be $1.1m, and according to AirDNA it would run -$40k/yr as an STR, and while local rent rates are high it would still run about -$2500k/m.It is such a cool and unique property I hate to let it go and would love to find a creative use for it that could at least carry itself (approx $6k/m+).

These can sometimes offer better cash flow, especially if you’re in a family-friendly area with unique features like extra square footage, an ADU, or flexible layouts.

I believe CA market in general is expected to increase by 4-5% but SF is unique. 

In my experience, finding deals with strong potential for cash flow, often means digging deeper into off-market opportunities or unique property types that traditional models overlook.

People follow those who have unique takes and are original.

.- My Resources / Constraints: I'm in a by no means unique, but perhaps less common situation for those getting started; I'm a somewhat senior software engineer at a tech megacorp and should be able to save a couple of down payments per year for lower priced houses (100-200 in my area), or perhaps one medium priced house (300-500).

Congrats on being a unique offering for the area. 

Maybe my experience is unique- maybe not.

Plus, living in the property gives you the unique advantage of understanding it inside and out.. making you a better landlord when you eventually rent out all the units.If I were you, I’d prioritize properties with room for rent increases or small upgrades that could boost value.