When I was in US last year, I bought my ipod from the online applestore. Before that I have seen only the big ipod models, and never used the "horrible" iTunes software. Since I didnt want to waste too much money on an mp3 player( btw, I had just lost another mp3 player, which I had bought 1or 2 months back)i decided to choose ipod shuffle, which was $100 at that time.
The small pack came to my hotel address in 2days time and I was happy. I thought I would be able to use it the sameway I used my other mp3 player (just copy & paste the mp3/wma files from laptop) but it came with its own software to copy files. Somebody told me that it is for preventing piracy!!! but I still dont understand how iTune is preveting piracy. Unlike any MSFT tool interface, I found ITunes very difficult to use. The only easy option I found was "autofill" which will copy all the mp3s in your system (or whatever playlist you set somewhere) to the ipod.
Things went well for me for a few days, but after a few days, somehow it started misbehaving.
I dont know if I have done something wrong, but when I plugged in the ipod to the laptop, it failed to detect it and after some firmwere update, it came to normal. By that time I have lost all the songs I copied to the ipod. That was just a beginning. after that the behavior of the ipod was very random. Sometimes it works, but sometimes it showed the LED blinking in orange color. Then I have to do a firmware update, which again needs me to copy songs from my computer. Sometimes I (infact my friends too) spent hrs to recover it and copy songs to it. I have aproached the Apple shop in bangalore, to figure out the problem, but they didnt have a solution. They copied some songs using the Apple system (Apple OS), but in a few minutes the ipod stopped working.
If you are plannign to buy an iPod shuffle, I would not advice it. May be the problem I was facign was unique and specific to that piece of gadget, but still I found too much difficulty with the software and tools associated with it.