One common problem faced is difficulty in understanding the iTunes library syncing concept. Use a run once tutorial or do some simplification to the process so that users don't accidentally delete their collection. It nearly happened to me once.

Apple products would find wider acceptance if they weren't so tightly linked together. For instance, to put in a song into an iPod you need to use iTunes. This becomes an issue on platforms which don't have iTunes, such as Linux. I for one, would have considered buying an iPod if not for this problem.

There are hardly any Apple stores in the country. Even with the wild success of the iPod, Apple has not opened up enough stores when in comparison its competitors have a big presence.