Berkeley is dirty, expensive, and everything closes at 9pm sharp. Anticorporatism is strong so most shops are coops or expensive food stores. The college environment and the college kids somewhat make up for it, the atmosphere is hard to beat.
San Francisco is crowded, expensive, and it's a second-rate NYC. But the proximity to everything and everyone again makes up for a lot, especially for cuisine and nightlife. Driving is pain, housing is a pain.
Milpitas is cheap, full of housing, but next to the city dump. It smells in the summer and since there's so much suburban sprawl, you'll drive for half an hour before reaching the highway. Everything closes early too, there's no downtown or nightlife.
Mountain View: tract homes suburban sprawl. Mountain View has one long strip called Castro street that masquerades as a downtown on certain days. Other than that it's just old 60's tract housing style (you'll find this to be the case for almost all of Silicon Valley).
Sunnyvale is like a pseudo commercial zone where all the warehouses and tiny offices are. Imagine playing SimCity and watching your purple zone languishing. That's Sunnyvale. It's definitely cheaper though to live because of this effect. There's a Fry's and Costco here, meaning you don't need to go anywhere else.
Cupertino/Saratoga has one big hit: Apple. There's no downtown, everything closes at 9pm sharp. Cupertino is essentially where everyone commutes back to after working in SF or Sunnyvale. There are an abundance of police officers because of the odd arrangement the city has with the county to generate revenue. Saratoga is up in the hills which is pretty but basically excludes anyone without a seven digit network.
Palo Alto is schizophrenic in that it doesn't know whether it's a farm town, college town, ritzy retreat, or corporate shill. Stanford is here and the surrounding area outside of Stanford is great. Sand Hill Road is right outside, there's a strip that act as the downtown, significantly longer than Castro. But because of Stanford it attracts quite a lot of companies to move here which in turn forces house pricing through the roof. Facebook is based here and they pay their employees an extra $600 to live within a 1 mile radius, meaning your chances are next to nothing to get a nice place. Watch out for East Palo Alto, that's not a place you want to be.
Santa Clara is like the ice cream center of a cake. It slowly melts into either layer but in the mean time it acts as the barrier between the sponge up top and the ghetto area on the bottom. This is where most people go because of the lower housing pricing due to market pressures. It's not a bad area, but then again it's not the sunny disposition you would expect California to be known for. This is also where my stolen car ended up at. Twice.
East San Jose. This isn't meant to be racist: east San Jose is where most of the poor live, there's a huge Mexican and Vietnamese community here. This is also where the low-rent and section-8 apartments are and where most of the illegal immigrants will bus from to find work at Home Depot in other areas. This isn't in any way to degenerate them, but this is just how the city is broken up into. Go more east and near the mountains and you end up at this ritzy and rich community called Silver Creek where they built thousands of big houses. You can drive for an hour here and still not see the main highway.
San Jose itself is huge. In fact, it's bigger than San Francisco, ranking itself as the 3rd biggest city in California. There's a downtown, but it's not as glamorous as say New York nor LA. Plenty of clubs to go to but it's almost always full of cop cars, low riders, scrapers with big wheels, and sound system that's enough to shatter glass. Quite a lot of companies are here though, Adobe for one, and the recent clamor for city living has caused quite a few skyscrapers to go up for loft living and the like. Prepare to pluck down more than $750k for a 900sq ft loft with sky high windows that look directly into a depressing airport. Oh, at least they have the courtesy to shut off the airport after 9pm (apparently everyone sleeps at 9 in Silicon Valley). There's multiple museums though, but they have enough content to last you through maybe 3 weekends.
This turned out more pessimistic than I had originally intended it to be. It's not to say I hate Silicon Valley, but the wide-eyed optimism has worn off. Don't think it's a dreamland, it's just an certain area where lots of people have moved into. The new trend now is to tear down unoccupied commercial zones (caused by the first dot-com boom) and remaking them as condos. Expensive condos. It's only getting more and more people to come in. Traffic is annoying. Stuff is expensive. There's houses everywhere. And most areas lack charm.
So in summation, where would I go?
With a bit more money saved up, I would much prefer Palo Alto, it's by far the best area, a 30 minute drive to the City (that's what we call San Francisco) and close proximity to Mountain View. If I just need a cheap place to stay? Santa Clara. If I want to live the California life? San Francisco. If I have a family? Cupertino. If I really really really want to have a house? Milpitas.
Don't take this post as gospel though. I've only been living here for 15 years and can't say I have truly captured ever nuance of Silicon Valley.
Addendum: Oakland. It's in a renovation stage. What used to be a horrifying place to live at is now being revitalized for business and as a contra to SF. The popular trend amongst my friends and smaller startups is live in SF or Fremont/Union City and rent an office in Oakland. You can find a huge 1500 sq ft open loft/warehouse type office for less than $1.50/sqft. I still wouldn't live in Oakland though.
You didn't mention Redwood City. This is where I moved to four months ago, and I love it. The downtown is small, but beautiful with many restaurants most of them have outside seating because the weather is so nice. Actually, Redwood City uses the slogan "Climate best by government test". And I would agree; we got only 3 cloudy days in the last 4 months. It's not too hot and not too cold. And, it's not as expensive as other places. As for location, it's close to the 101, and it's half-way between San Francisco and Sunnyvale, so you're not too far for any event in the city or the valley.
In my mind I kind of lumped Redwood City, and that whole Atherton area, in with Palo Alto. Redwood City indeed is a very nice place, there's decent housing, a friend of mine whose parents are pastors were able to buy a house with a pool, and there's this atmosphere around that particular area that's just unique. I think it's a combination of expensive cars, luxury housing, and smart people that makes me want to do better.
You missed the East Bay beyond the mountains (San Ramon, Alamo, Lafeyette, Pleasanton, Walnut Creek) and Marin. Less expensive than Saratoga and much better places if you have a family than Cupertino or (shudder) Milpitas. There are quite a few large companies in both places ( Fair Isaac, PeopleSoft, Sybase, Chevron )
Hm, I only scanned this but it seems fairly accurate. It's completely void of all the pluses of those places though. After our summer in Cambridge, we moved from Milpitas to San Francisco.
San Francisco is crowded, expensive, and it's a second-rate NYC. But the proximity to everything and everyone again makes up for a lot, especially for cuisine and nightlife. Driving is pain, housing is a pain.
Milpitas is cheap, full of housing, but next to the city dump. It smells in the summer and since there's so much suburban sprawl, you'll drive for half an hour before reaching the highway. Everything closes early too, there's no downtown or nightlife.
Mountain View: tract homes suburban sprawl. Mountain View has one long strip called Castro street that masquerades as a downtown on certain days. Other than that it's just old 60's tract housing style (you'll find this to be the case for almost all of Silicon Valley).
Sunnyvale is like a pseudo commercial zone where all the warehouses and tiny offices are. Imagine playing SimCity and watching your purple zone languishing. That's Sunnyvale. It's definitely cheaper though to live because of this effect. There's a Fry's and Costco here, meaning you don't need to go anywhere else.
Cupertino/Saratoga has one big hit: Apple. There's no downtown, everything closes at 9pm sharp. Cupertino is essentially where everyone commutes back to after working in SF or Sunnyvale. There are an abundance of police officers because of the odd arrangement the city has with the county to generate revenue. Saratoga is up in the hills which is pretty but basically excludes anyone without a seven digit network.
Palo Alto is schizophrenic in that it doesn't know whether it's a farm town, college town, ritzy retreat, or corporate shill. Stanford is here and the surrounding area outside of Stanford is great. Sand Hill Road is right outside, there's a strip that act as the downtown, significantly longer than Castro. But because of Stanford it attracts quite a lot of companies to move here which in turn forces house pricing through the roof. Facebook is based here and they pay their employees an extra $600 to live within a 1 mile radius, meaning your chances are next to nothing to get a nice place. Watch out for East Palo Alto, that's not a place you want to be.
Santa Clara is like the ice cream center of a cake. It slowly melts into either layer but in the mean time it acts as the barrier between the sponge up top and the ghetto area on the bottom. This is where most people go because of the lower housing pricing due to market pressures. It's not a bad area, but then again it's not the sunny disposition you would expect California to be known for. This is also where my stolen car ended up at. Twice.
East San Jose. This isn't meant to be racist: east San Jose is where most of the poor live, there's a huge Mexican and Vietnamese community here. This is also where the low-rent and section-8 apartments are and where most of the illegal immigrants will bus from to find work at Home Depot in other areas. This isn't in any way to degenerate them, but this is just how the city is broken up into. Go more east and near the mountains and you end up at this ritzy and rich community called Silver Creek where they built thousands of big houses. You can drive for an hour here and still not see the main highway.
San Jose itself is huge. In fact, it's bigger than San Francisco, ranking itself as the 3rd biggest city in California. There's a downtown, but it's not as glamorous as say New York nor LA. Plenty of clubs to go to but it's almost always full of cop cars, low riders, scrapers with big wheels, and sound system that's enough to shatter glass. Quite a lot of companies are here though, Adobe for one, and the recent clamor for city living has caused quite a few skyscrapers to go up for loft living and the like. Prepare to pluck down more than $750k for a 900sq ft loft with sky high windows that look directly into a depressing airport. Oh, at least they have the courtesy to shut off the airport after 9pm (apparently everyone sleeps at 9 in Silicon Valley). There's multiple museums though, but they have enough content to last you through maybe 3 weekends.
This turned out more pessimistic than I had originally intended it to be. It's not to say I hate Silicon Valley, but the wide-eyed optimism has worn off. Don't think it's a dreamland, it's just an certain area where lots of people have moved into. The new trend now is to tear down unoccupied commercial zones (caused by the first dot-com boom) and remaking them as condos. Expensive condos. It's only getting more and more people to come in. Traffic is annoying. Stuff is expensive. There's houses everywhere. And most areas lack charm.
So in summation, where would I go?
With a bit more money saved up, I would much prefer Palo Alto, it's by far the best area, a 30 minute drive to the City (that's what we call San Francisco) and close proximity to Mountain View. If I just need a cheap place to stay? Santa Clara. If I want to live the California life? San Francisco. If I have a family? Cupertino. If I really really really want to have a house? Milpitas.
Don't take this post as gospel though. I've only been living here for 15 years and can't say I have truly captured ever nuance of Silicon Valley.
Addendum: Oakland. It's in a renovation stage. What used to be a horrifying place to live at is now being revitalized for business and as a contra to SF. The popular trend amongst my friends and smaller startups is live in SF or Fremont/Union City and rent an office in Oakland. You can find a huge 1500 sq ft open loft/warehouse type office for less than $1.50/sqft. I still wouldn't live in Oakland though.