* Difficulty to make real friends; meeting a lot of d-bags.
* Traffic/waiting for everything.
* Public transit in any major US city (except perhaps NYC) -- everyone always complains, even if it's decent. (IMO, SF's is at least decent.)
* Cities have rich areas and poor areas, safe areas and dangerous areas. West coast cities have homeless people.
* Seemingly few non-touristy things to do during the day (in the city at least), outside of the regular coffee/eating (and if you're not into watching sports).
I also second that if you're unhappy with where you live, you may just be unhappy with whatever you're doing. But, it is genuinely hard to meet friends and potential dates when you're new to an area, don't know anyone, and aren't in school. Give it a year and put yourself out there!
Would it be reasonable to ask you to write a comparison of the two? I'm sure I'm not the only one who would be interested in a first-hand comparison as both are popular techy destinations but seem like fundamentally different cities.
If I can find a way to discuss this abstractly, I for sure will.
For now, you can crawl through my HN comments, where I've talked about Portland a bit. Here i did a bit of a comparison of SF/PDX, though it was mostly about Portland:
Not sure if I've taken in enough of the new city to write an in-depth comparison. But if there's anything you want to ask, feel free.
My answer is the same as what I wrote above cities. Whatever works best for you. It's totally personal.
For me, it's a problem, but for other people, it's not at all, and I'm not mad at that.
Diversity can mean lots of different things. For some it can mean people from different countries, different genders, different schools, different parts of the country.
For me it mostly means different backgrounds. I basically seriously dig it when the people i discuss tech stuff represent the world i otherwise live in + with.
(As Alex hinted at with "1st world problems...") Some can people stand in a circle at a launch party where everybody talks about their favorite ipod headphones for 45 minutes and totally dig it, and others can walk away from that feeling really out of place. Neither one is wrong or right, but it is quite easy to slip into an intense, concentrated subculture in quite an exceptional way.
(the second part of your question: startups vs big tech co's)
I go down to SF a lot for conferences. I notice more diversity and different backgrounds at events from large companies (like VMworld) than i do at open source things, i wish that were flipped, as i do more open source stuff than corporate stuff, but it's cool. Either way i get a lot of good info from the events.
I agree with most every criticism he has of San Francisco, but maybe don't hold the same vibe of judgement.
Ultimately, he seems to be on the right track, that San Francisco is not working for him. That's really all we should focus on when deciding where to live. Look inside yourself, think of what you need, and what type of place makes that easier to achieve.
Unique Challenges for him
I imagine holding a high-profile job at red-hot company (Twitter) in San Francisco/Silicon Valley could be claustrophobic socially and physically. Also, a bit of a monoculture, intellectually, as he described. (In the middle of a really diverse place, I've witnessed an eery lack of diversity when attending some SF tech events.) And he totally fairly introduced his blog post as such (for young tech types). But many tech types might be able to overcome some of the challenges he had, just because it's extremely unlikely they have the same work + media + community demands that Alex has.
Anyway, I'm not really disagreeing with anything he said. His post was great. Also, if he reads this, I want him to not stop writing things that actually state an opinion, no matter how rowdy reactions get. :D
San Francisco workarounds (for everybody else)
If you're stuck in San Francisco, and getting annoyed by things, i have some workarounds:
* Live "on the other side of the hill." I lived in the inner Richmond district (the San Francisco neighborhood, not the city). Every time there was a massive fair/festival (mentioned in the blog post), I didn't know about it.
* Living on the other side of the hill also changes up the sorts of people you live around. Less dot-commers.
* Take BART/Car out to the rest of the Bay Area. Cities like Fremont and Redwood City have lots of interesting destination to get you out of the bubble (indian movie theaters, streets where you HAVE to speak Spanish (as a speaker of Spanish, a pleasant experience for me.)).
* Seriously evaluate whether your friends are d-bags
* Seriously evaluate whether you sometimes are a d-bag
* If you are for sure not a d-bag, and are sure your friends are not d-bags, avoid places where d-bags are. You are who you are around. You are probably ruling out places in the Marina right about now. Sorry, not agressive enough. Even really cool places on Saturdays might be making you sick.
* Make sure there is meaning in your life. This is not a San Francisco thing, but almost everybody I've witnessed who is extremely unhappy with the place he/she lives, has something else pretty heavy going on in his/her life. Real talk.
I left San Francisco extremely annoyed with the ridiculous real estate situation, my quality of life, and lots of other stuff. All those opinions still hold true, but I now sit back and see some things I did to make life more difficult for myself.
After experiencing the civic magic of Portland, I'm more patient, interested, and appreciative of ALL city landscapes and experiences, including San Francisco's. I could easily see moving there again one day.