We lived in Dublin for 20 years; through a lot of highway construction and growth:
We loved Pleasanton. We loved visiting S.F.
I cannot imagine doing both!
If you are bound and determined; I would use Bart, not driving:
You are looking at 1 1/2 hours, on a good day!
Unless you are going in at 4:00 and getting off at 2:00.
And this is experience talking;
First we lived in Sunnyvale and I commuted to South San Francisco, up 280.
Then, we moved to Dublin while I was working in Mountain View.
I've got the scars.
The secret is having a big, comfortable car, (gas mileage is a lot less important) and I listened to books-on-tape; quite a few books over the period.
Good luck and may God bless