This is pretty doable, and shouldn't be too exhausting. A few points to ponder:

SJC area hotels can get very expensive during the business week. You might consider working out an arrangement with one for a rate certain for a time period certain (and perhaps the hotel can store a bag for you).
If your SJC flight cancels, you can probably hop on an SFO flight and still get to the office in time. You may also find yourself on WN from time to time.
There will be times when you just don't make it, for reasons on either end.