Is Oakland the least shitty place to live in for SF work?
tl;dr: Yes.
LONGWINDED EXPERT MODE: Depends on what you call "shitty" and what you want your commute to be. Living in SF itself is stupid expensive, South SF only slightly less so with a huge drop in amenities and personality. Same again for San Mateo (though it has its points!) and more-so for Redwood City. If you're on the peninsula, living -AND- working near a CalTrain station can help, but if you're in tech, the hours don't make it easy to keep their schedule, and about once a month some shithead loses their vehicle or their life or both on the tracks; unlike Japan, there are not alternate railways to take to get home.
If you're off the south peninsula, any bridge in Silicon Valley (Hwys 80, 101, 92) is a
complete shitshow during commute times and, with flexible hours, commute times are not easily defined. 6AM? 10:30AM? Still garbage pace. I'd argue that Piedmont is a nicer area than Oakland, but I love the part of Oakland which borders on Piedmont but is not zoned as Piedmont. It's got a lot of personality and community spirit.
If you want utter suburbia, Milpitas will have you ward-and-juning it up in no time. Union City is track-housing and minimall central, but has enough immigrants that it is bound to eventually find a unique flavor. Its neighbor to the north, Hayward, should be renamed "Little Fresno."
