I grew up in Oakland, but haven't been back for more than a week in 10 years. So I can help you some, but not with everything.
In general, San Fransisco is kinda like the Manhattan borough of the metropolitan area, usually just called The Bay Area. The Phone Books all just say West Contro Costa County. Lots of ridiculously steep hills, cold fog every morning. Oakland is the slightly rougher (or maybe just less touristy) part across the Bay Bridge (think Brookland). It is buoyed by the fact that it blends straight into Berkeley to the north, which is an ultra liberal college town with an above average share of hippies and the occasional nudist out for a walk. North of that is Richmond, which is the middle class suburban area I grew up in. Well, technically I grew up in Pinole, the tiny town to the north that hasn't visibly changes in 20+ years and is known for its "timelessness" (which is the nicest way I can put it). That town ends rather abruptly into hilly graze-lands. The average resident would be aware of a painful commute from there to any of the main parts of town using either a parking lot of an interstate, or taking the back way around the hills to the Caldecott Tunnel straight into berkely.
North of SF there is some sparce-ish stuff on the inner side, and hilly park lands between you and the beach, but is more the stereotype california beach town type stuff than anything SF specific. South of SF I have much less experience with. Its got the main airport for the area (there is one in Oakland too, but its a pain to get in and out of). Past that it trickles out into various smaller towns and suburbs along the bay as most large cities tend to do, but I cant tell you much more than that.
If you go to SanFransisco and don't go to the Exploritorium, you've done something wrong that you will regret for the rest of your life. A giant hands-on museum. Lots of perception illusions etc. You know those Plasma Balls you see in Spencers and every mad scientist's lab? Invented just as a hands-on demonstration for this place. Loves me that place, and have never heard of somebody having less than a blast there, even when initially forced to go.
1)Was too young when I was there
2)Depends on mobility. There are some low income places in oakland, some slightly better ones nearer the university, or else a drive or Bart ride (what they call the above ground subway system) from the more fringe areas like richmond.
3)Downtown Oakland comes to mind. There are probably some areas in SF proper as well, but too much walking up and down those hils tends to suck quick.
4)Richmond. Anywhere works for middle class. Country Clubs in East Richmond Heights/Kensington up on the hills, and the Richmond Golf Club to the north, near the water.
5)Couldn't tell you, need a more specific area. There are tons of little corner coffee shops etc, but no widely famous ones i know of.
6)Definitely Hilltop Mall in Richmond for an actual Mall. Most other shopping is more street, storefront, or boardwalk type setups. Or you know, the Costco.
7)As a rule sure. Like I said, they have nudists casually wagging down the street, so a little wiccan twist isn't going to raise eyebrows. Last time I was there fairy talismans were common wall hangings in the bookstores and such. That being said, they are not nearly as much the laid back live-and-let-live sort of hippie as you'd expect, especially for a town with such and open and nearly legal pot industry. Far more often you get the cause-head activist hippies, which are by nature more forceful with their opinions and beliefs. But it would be more a personal level friction, rather than a group movement of belief. Unless they think you are going threaten the bunnies with mascara, or sacrifice that poor chicken, or something that set em off. Then they can get just as idiotically close-minded as any other mass of people.
