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I've started to feel this way, too, but I guess I'm more selfish: the things I want to do and the products I use mesh together really well, and I've stopped caring about other people's problems.

I feel bad for people who have hopelessly broken setups, but not bad enough to want to help.

While not the primary point of this article, I'm constantly amazed how much software collectively sucks. Why can't I just say "hey phone, here is my calender app. Sort it out between the two of you". Or another favorite: Why doesn't outlook give a big, fat warning if you open an attached document, edit it and save it? (it gets saved into the temporary directory, where it and all your edits gets promptly removed.)

There are so many tasks on a computer that are just fundamentally broken for a large number of users because they don't get the concept of files in folders and applications that interact with these files. Programmers (myself included) lazily assume this knowledge instead of thinking about what a user might want to do. "I want to listen to a song" shouldn't involve the user picking a nice place on their disk to store this particular song, and ideally the browser and music player just work together to 1) open the song and 2) make it available from within "music" whenever the user wants to hear that song again.

This is especially painful when having to explain to others how an overly complicated (which most of the time means dumb) piece of software (windows, itunes, any antivirus) works, and more often than not I resort to "just bring the pc over, and I can do it in five minutes for you". As a developer, I feel shame whenever I have to update my mothers iPhone or reinstall my grandmothers computer because we can't make something that takes their needs into account. (Regarding the last: ever tried globally enlarging text on windows for bad eyesight? It obscures so much text in incorrectly sized buttons that it might as well be non-existent.)

I agree, but aren't these fundamentally hard problems? Take your calendar example. You could solve that problem with:

* Standardization. Difficult, but possible, if you can convince the entities involved that it's a good idea.

* Machine learning. Unreliable, since even a human might have trouble bridging the gap between the phone calendar's idea of an 'appointment' vs the desktop calendar's idea of an 'appointment.'

* Future Magic. Only works in Microsoft promo videos.

Neither of the two serious solutions seems very good. Is there a better way that I'm missing?

Actually, most people don't seem to know this, but if you go ALL-Microsoft or ALL-Apple, everything pretty much works. The problem is, most of us don't want ALL anything, because neither company has a perfect solution for everything.
Yes, they're hard problems, but most of what we do is a cop-out, or as the OP says "whatever shoddy pile of hacks we’ve cooked up by then".

For example, I have to search for some obscure instructions to get my two Google calenders syncing with my iPhone that involves my either adding an "email" account, or manually typing in some ridiculously long "secret" url. Why can't I just open google.com/calendar on my phone and have it say "Hey there, want to add me to your phone's calendar? Click here!"?

I submitted this as a bit of a test. Just a few minutes before submitting this one, I submitted what I thought was a much more interesting story - http://news.ycombinator.com/item?id=3286509

It seems HN is more interested in blog posts by famous people than actual hacks.

It's especially interesting considering how much Marco is railing on HN lately, in an aside-from-nowhere in this post and on twitter.

He hates that HN brings him people who will criticize him, but at the same time every article he posts is voted to the top here, and whenever Instapaper is brought up in discussion it is revered.

"I’m accused of fanboyism a lot more these days, but only because Hacker News keeps sending huge waves of people here who tell me I’m an idiot."

It is true that, at times, HN can latch to technology "beliefs" as strongly as some political robot spews garbage in the HuffingtonPost comment section (whatever you do, spare yourself the pain of ever looking there).

This is because people naturally focus on their individual experience and bias, not large swaths of the population. It's the way people are wired. And, a lot of HN'ers are hard-core-anything-but-Apple for lots of reasons.

But I do think the discourse here is at least backed up with intelligent supporting arguments, not just knee-jerk opinion, even if it is myopic and individually anecdotal. And it is for that reason that I often find myself reading the comments here before I read the actual articles.

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I feel responsible for what I recommend so I'm careful with big claims. When I help I rather try to go with incremental improvements rather than "the" solution.