I also might be able to get us the room at Sip.

And this one cracked me up: "We were sipping lukewarm coffee from chipped mugs, half convinced we’d made a mistake."

I work but without the weight of the world on me at this job, I also fish more, and spend more time sipping whiskey just watching the sun go behind the mountains....

The mirage of get into Real Estate Investing, make ton's of money, get passive, do nothing, sip cocktails on the beach and professionally vacation the rest of your days sounds great, unfortunately it's a mirage. 

This idea of FIRE in your 20s (dare I say 30s and even 40s) makes zero sense - the idea is propagated by what we see on social media (Some 26 year old walking by his G-Wagon and sipping martinis on the beach 300 days out of the year talking about his billions in RE).

How will you manage them while trying to be "passive" and sitting on a beach sipping Pina Coladas?

You weren't six  states asway sipping margarita on your yacht in the marina.

If Planning does determine the existence of your ground floor unit, it will require you to legalize the unit through the existing Planning code process assuming zoning supports the third unit OR using the new ADU program making your fast track condo conversion a passing dream.With regards, to some of your latter comments and questions:1) Any un-permitted work (including corrections) is not a good idea as a quick compliant from a neighbor can bring an inspector knocking on your door with a NOV especially in the current environment where everyone is SIP.2) Legalizing existing constructed spaces can be hit and miss based on the inspector you get.

An old tv infomercial championed you to get rich quick and sit on the fan tail of a Luxury yacht sipping a tall cool drink surrounded by swimsuit clad models.

I wanted to post about how, "I enjoy long walks in trap houses" and how I enjoy "sipping red wine while I watch my rehab go over budget"hahaBut yes you should systemize your search.