I have a BART card with a chip, so at least we're making progress (the downside is that it's not compatible with any other transit provider). Hopefully we'll see a combined card down the line to include things like MUNI or Golden Gate ferries.

My Citi Dividend card has PayPass, but the only places I've seen the logo around here is at McDonalds. I've popped in there for wi-fi access when traveling and put $2 on it for a Diet Coke. I agree that the cashiers don't seem to know about it and are surprised when a receipt pops out of the register without them doing anything.