Well, I’ll bite…
I am a big fan of my iPod and I liked it so much that I decided to get a Mac afterwards.
First I switched to iTunes for my music player on my PC. Why? I liked several features.
Firstly, you don’t need to manage your MP3 structure anymore. If you want to burn a CD from your MP3s then it has that function already integrated. For me, I play songs, and would occasionally copy them to a cd. If you download songs, you can have it automatically copy them to a central folder every time it is played with subfolders for the album, etc. Secondly there is the beauty of “smart playlists.” You can have a specific playlists that plays songs that you have listened to more than 50 times but not in the last month, for example. There are countless combinations available for listening to stuff that you haven’t gotten around to recently. They update automatically if you want, and when you listen to a song on your iPod it will automatically update with iTunes these stats along with ratings you might give while listening on your iPod.
So for me, the iPod + iTunes combo is my music nirvana. Anytime I add songs from a CD it will automatically fetch the names and import them to a variety of formats including AAC, MP3, WAV, and apple’s proprietary formats.
You also get the music store with is very addicting. But this is a very typical apple approach to everything. They sort of pidgeonhole you into doing things their way, but in the end, it works pretty well. Before I used winamp and I would make a playlist by looking at the MP3 files or using a similar library function in winamp. But for some reason I just like iTunes better. Anytime I download a song it gets instantly added to my library in one central location if I ever needed to back them up.
But I like to keep things simple on the tech side of my life. My cellphone doesn’t have a camera, and is pretty basic. I don’t want anything from an MP3 player than that it plays MP3s. The interface is also very good as well.
Also, all iPods come with a one-year warranty I believe, and Apple will basically send you a new one pretty quickly if necessary.
If you don’t get an iPod, I’d suggest you use an iTunes compatible player. This is the next best option I believe. But in any case, i suggest you try iTunes for the reasons I have posted above. In Itunes you can drag songs as if you were looking at the real files*. So if you have your MP3 player working in hard disk mode, you can simply drag the songs from iTunes directly to your disk and they will copy from whatever location they are in. Give iTunes a shot, and forget about keeping your collection organized. You won’t need to. It does all that you could want to do with music. Also, if you have a lot of CDs it is great to use iTunes to import them as there is an option that will automatically rip the CD when you insert a disc and then eject it making for very fast batch conversions.
*This is the way it works on a Mac, at least.