Specifically, I meant that usually there's a reasonable work-around. Something you can probe, inspect, and otherwise work with. In this case there really just isn't anything useful at a high level.
A better term might be it seems to violate the Law of Least Astonishment, but from the hacker perspective instead: I have a device that's really just spoofing acting like a storage device. There's a lot of side trips that normally can be taken to work around this, and each are the same sort of no-op, since it's not for real. This sort of thing was common for the old 'dumb' phones, but it seemed like it was because they were too dumb to behave properly; now here's a smart phone being dumb. It's a bit unexpected, at least for what seem like obvious things like "add mp3". But there we are. The whole time there's a feeling of "gosh, surely there's a better way" and there just really isn't: install iTunes and let it do whatever it wants, or you just don't get to put that mp3 on your phone.
And wanting to avoid installing iTunes isn't pointless. I mean, you may not see it, but there are certainly reasons not to. Heck, just failing to update iTunes was useful for a few years due to some odd DRM workarounds (mostly for a WinAmp addon that read iTunes music files). Besides, it's fairly invasive - you may only use it rarely, but it installs a couple services and tries to jump in when the phone connects (all can be administered, but it's a pain cleaning up that mess). While I've finally come to just tolerate it, I don't appreciate it.
(Perhaps I should use counterintuitive? I would hope that would get the same idea across without somehow triggering offense. The problem I'm describing is of expectation and should be orthogonal to intelligence. There's a lot of subjectivity to it, but no reason to take offense. Mindsets filter, so why would a hacker find the same things intuitive as your average user?)