As someone whose three best friends live in SF, I can state that I consider the Bay Area an awesome place in every respect except one. It has some of the best food in the world, acres of beautiful parks and beaches, convenient to use public transportation, easy access to wine country/national parks, an active sports culture, great weather, fantastic museums, exceptional local beers, a wide selection of music/cultural events, and an active but not insane night life. I visit often and love it every time. That said, the price of housing is a moral and practical nightmare, pushing thousands into homelessness, creating a public mental health crisis, making the city increasingly inaccessible to members of the middle class, and transforming much of it into a playground for the elite at the expense of longtime residents. But there are a ton of great things about the city that simply have no appeal to Jeff/Dan and it's one of the greatest places in the world if , you know, you ignore the massive inequality at the heart of the city.
Incidentally, I was shocked a few weeks ago when Dan said on the Bombcast he'd only been to Oakland a couple times. It's a cool city that he'd probably prefer to SF.