1. Chinatown is really filled with tourists or elders who are too poor to go to better places on the west side of SF or out in the suburbs (I grew up and live around there). That said, R&G Louge is pretty good cantonese but well-known to tourists and concierges and nothing amazing if you've eaten at top places in China or, especially, Hong Kong. For dim sum, I think everyone agrees Yank Sing's two locations downtown are the best in San Francisco, and the most expensive. In Chinatown, Lai Hong Lounge is a step down in both regards, but not bad.
2) Slanted Door is not worth the wait or the price—you can really do just as well at modern Vietnamese places for 1/3 the cost as long as you don't care about fancy service and surroundings. Back when Slanted Door was at its original location in the mission it was a lot cheaper and, frankly, more special.
3) Yeah, most places in North Beach are laughable imitations of tourist food. The only place I know of that isn't bad is Park Tavern, which is really just a classic American bistro (it's the team behind Marlowe).
4) Ad Hoc is fine. If it wasn't for the The French Laundry/Thomas Keller brand name I don't think it would be as highly regarded.
5) Bottega. Not really worth the money, though not bad or anything. You can do better for the same price or less when it comes to fancy Italian in the Bay Area.
6) Mission Chinese Food is totally doable. Either go early/late or take out/deliver, as dunstable suggested.
As to your other questions about first dinner and Mission/Castro/Haight, do some of your own research. There are tons of posts here and maps on sites like eater.
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