> I knew Los Gatos was well known for being an incredibly wealthy zip code but I had no idea it was pretty much the #1 most expensive city in the USA.

How is Los Gatos remotely the #1 most expensive city in the USA? Even just in the Bay Area, there are many pricier places (Atherton, Woodside, Portola Valley, Palo Alto, ). Then there's Beverly Hills, many other parts of LA, NYC, Hamptons, Cape Cod, etc.

Regardless, Los Gatos pretty close to much less-expensive areas, including areas like San Jose, which have lots of dense housing. These areas are pricier than most of America, but they're among the more affordable parts of the Peninsula/South Bay.