I always hated how stupid it makes adding a few songs to an existing device. Half the time it wants to re-sync everything and wipe the device while doing it.
No, just ill-informed. You can re-download your purchases (which are DRM free) from the iTunes store on to your device. There is absolutely no need to use iTunes to manage an iOS based device. Not for registration, backing up or adding media.
Clicking the back button after going to this article prevents you from returning to HN, but rather sends you to jskicks' front page and re-opens the article.
Really shitty behavior. Or is this supposed to work better on mobile?
You've got to start somewhere. More often than not you start with the easiest option and find that you're knee-deep in crap a ways down the line. If all you care about is ease-of-use over learning opportunity you might as well default to Windows with whatever flavor of Visual Studio you can get.