San Jose is the heart of Silicon Valley. The bread basket of the dot-coms. The innovation engine that drives this country. It's also a shit-hole.
My real keys for determining whether I want to go some place boils down to these two questions:
Why?
For one, hotels are $200 a night, and that's for the run-of-the-mill. Normally this will be conviently located no where near where you want to be, and is booked solid because of the Left Handed Bit Flippers Convention.
Additonally, traffic is a nightmare. You have no idea what rush hour is like unless you're coming from Boston or New York.
When it comes to architecture and pure visual beauty, most cities has something comparable to San Jose. Normally they call them ghettos or The Projects. The entire city of San Jose is located on the 'Other Side of the Tracks'.
"What is there to do in San Jose?"
"Well, you can drive over The Hill to Santa Cruz, or maybe down to
Monterey"
"Huh?"
"Or you could drive up to San Francisco."
"What? Hello, geography boy! Those are all cities that are NOT
San Jose"
That's right, the locals all suggest that if you're in San Jose looking for something to do, you should leave San Jose!
Just about the only thing to do in the city is to visit the Winchester House. This is the house that the heir to the Winchester (of gun fame) had built under the direction of her spirtual advisors. I think they must have been Johnny Walker and Jim Beam.
Personally, I think you should prepare for your trip to San Jose by getting out your Rand McNally road atlas, examine the San Jose area, and then repeatedly beat your head with the atlas until you either get some sense or lose consciousness.