Back in May I won an iPod, and recently I became an iTMS customer (only to try it out since they’ve only just recently released Canadian version). So far my experience with the two has been relatively good. The iPod is slick and easy to use, which everyone already knows. iTunes is alright, but runs like crap on my aging P3-450Mhz machine.
The only thing that seriously pisses me off about the two is the DRM restrictions. Specifically, if anyone comes out with some amazing music player a year or two from now, I wont be able to take any iTMS music purchased onto the new device unless it supports Apple’s DRM (and how many players support Apple’s DRM? 4: iPod Generation 1, iPod Generation 2, iPod Generation 3, and iPod Generation 4). I understand the desire to not want me to give away free copies of music I’ve purchased to the entire population of the internet, but the restriction to what devices and which software I can use to listen to what I’ve purchased just pisses me way off.
All other things considered equal, the ease of playback on as many different systems (including competitor’s hardware) would be the number one deciding factor for me when choosing a future device.
Incidentally, if anyone is looking for a plugin for Winamp (the only media player that I use with any seriousness) that will allow them to playback their, legally authorized, iTMS music, you can use this one here, providing you leave iTunes installed on your machine. It works fairly well.