You have some good points, but some of them miss the mark. I entirely disagree with you sentiment that "you have to take the bus (or ride a bike)" is a downside. I consider this a major selling point to SF, you can get drinks with friends and not have to worry about driving under the influence. Almost every other city I have been to, you either need a DD, or you have to pony up a ton of money for a cab.
Regarding the old houses, roommates, and homelessness, by themselves none of these are really that big of a deal, and are probably pretty common in any major city. What is a little absurd (and you sort of alluded to this), is that we are paying some of the highest rent in the country, for these 'privileges'. However, I imagine most people who live here, including myself, don't exactly look at it that way. Instead, we look at it as we are paying high rent, for the privilege of living in SF and all it's perks (good jobs, active social life, etc..), and the old houses, roommates and homelessness are just a part of SF life.
I actually agree with what you're saying, I was more responding to people I know (and/or people that I see post here from time to time) that put SF on a pedestal, and seem to have convinced themselves that the downsides to SF are actually upsides.
I always ride the public transport when I go to SF, it's a great convenience and much less of a pain than driving up there and around there. I wasn't saying that public transport in SF is a bad thing (quite the opposite), but rather that it's often the only choice.
Like, even when it would be way, way more convenient for any number of reasons to just drive to wherever it is that you're going, various factors (parking, traffic, whatever) make it just too much of a pain. Even just owning a car when living in the city can be too expensive and more trouble than it's worth. I do see this as a downside to living up there (or just visiting), even though I would still ride the public transport most of the time anyway.
I know lots of people that live in SF and don't have a car (or in some cases even a valid driver's license), and they will swear up and down that having a car is totally pointless and why would anybody ever do that and what the hell is wrong with you anyway, do you enjoy filling up your tank with evil every week? :) But they spend 100% of their free time wandering around SF. It's not as feasible for them to go on day trips or weekend trips up and down the coast, or get out in the wilderness (at least, out beyond the reach of the bus system), so they just don't. They just hang around SF all the time, which is a rather wonderful place to be stuck in, but they are stuck there nonetheless. I love going on long drives and exploring all the remote corners of the Bay Area and beyond, and I couldn't imagine life any other way.
Regarding the old houses, roommates, and homelessness, by themselves none of these are really that big of a deal, and are probably pretty common in any major city. What is a little absurd (and you sort of alluded to this), is that we are paying some of the highest rent in the country, for these 'privileges'. However, I imagine most people who live here, including myself, don't exactly look at it that way. Instead, we look at it as we are paying high rent, for the privilege of living in SF and all it's perks (good jobs, active social life, etc..), and the old houses, roommates and homelessness are just a part of SF life.