1. Wealth: Dean lives in a multimillion dollar mansion on Alamo Square that he bought for $1m in 1999. He has no loan on the property as covered in his candidate disclosures: https://public.netfile.com/pub/GetDocument.aspx?ref=7907215a...
And THC does not pay its attorneys nearly enough (just cracking 6 figures in 2020) for that kind of wealth: https://nonprofitlight.com/ca/san-francisco/tenderloin-housi...
I can find references for his Sonoma estate later, but his parents were wealthy New York merchants: https://www.nytimes.com/1962/02/12/archives/linda-rothchild-...
In general, when you have an entire family of social workers who attended elite East Coast private school for the first 22 years of their lives living mortgage-free in multimillion dollar homes, you should assume generational wealth: https://www.legacy.com/obituaries/nytimes/obituary.aspx?n=le....
It’s funny that this information doesn’t make it into the Wikipedia page.
2. Blocks housing: Prop I was opposed by the city economist because it was effectively a per-unit tax on new apartment development. Most apartments are developed and operated by separate entities, and it is common for developers to sell constructed developments to apartment operators. IIRC, the estimate was an over $30k/door tax on new apartment construction on top of the existing impact fees. Very few transactions over $10m are purely speculative or for cash flow (it’s too lucrative to just hold with Prop 13); most involve some development objective. The estimate was a 20% annual reduction in apartment construction annually (https://yimbyaction.org/endorsements/san-francisco/).
Prop K is a canard — it’s not even clear the city as met the quota allowed from the previous Article 34 authorization in the 90s. The primary reason there’s no public housing in San Francisco is funding, not voter authorization. It does look good to low-information outsiders, I admit.
Dean is famous for “blocking housing” in indirect ways. He advocates for inclusionary zoning at percentages where a project will never be financially viable without outside subsidy, like the Divisadero gas station project. In power, he blocks projects directly (https://socketsite.com/archives/2020/06/impact-of-modern-inf...) or through the addition of expensive, capricious delays (https://www.sfexaminer.com/news/supervisor-seeks-to-pause-hu...).
3. Never had a job: I think it’s common for this kind of pejorative to mean “only worked for employers who are not incentivized to perform” (i.e. public / non-profit sector), not literally “never earned wage income.” Certainly applies to Dean.