(a) It should be automatic -- if they have the tech to enforce parking like a witch hunt, they should have the tech to just charge people for parking automatically just like Fastrak and everything else. Just have parking meters look for a Fastrak transponder and charge that account for parking, and also automatically send texts to the phone number and e-mail associated with the Fastrak account if time limit is reached. Make the city a good UX. Parking payment should be a zero-effort operation. I shouldn't have to make a wager on how many minutes I'm going to take to finish my meal and risk wagering too many minutes (overpaid) or too little (get fined). Just charge me according to my actual usage.

(b) Parking signs are too goddamn hard to parse, that's the real problem.