Also consider whether you’ll want to get into podcasts. I love my iPod and I’ve learned to live with what I don’t like about iTunes, but its ability to seamlessly find, update, and organize podcasts would be worth it even if it didn’t also hold my >120GB music collection.
Other players may handle podcasts as well, and it’s always possible to sync them manually, but iTunes is really what they’re designed around.
The Sansa supports drag and drop as well. I would strongly advise against a Sony product. Over-priced, under-featured, and Sony’s DRM ethic makes their products suspect.
I’m not saying not to get an iPod. I’m saying, let’s find your need. Why do you need a portable MP3 player at all? Will a computer work as well? How will you be listening to these? Do you want a stereo hookup?
If you want simplicity, the iPod is for you IMO. If you’re kinda tech-toy oriented, you can find other options that give you more flexibility.
I’ve owned a Creative Zen Micro (6gb), which I liked a lot, and an Ipod Classic (80gb), which I also like although it doesn’t sound as good.
Mp3 players typically come with conversion software, which is typically what you’ll use, but you can use any ripping software you like. 128kps is a typical rip speed, and it’s a bit low in quality - on higher end audio equipment the difference is obvious over 160kps, which is cd quality and my preferred speed. The quality of the rip, the quality of the headphones or speakers, and the quality of the player itself are all important in determining how good the sound is. Mp3 players can hold anywhere from a few dozen songs to tens of thousands. There’s not that many big name players that have huge storage space though, and the smaller ones do sound good. My Zen Micro 6gb sounds great, has no games, pictures, or other frippery, and is very, very easy to navigate and use.
The ipod classic has a huge amount of storage space, a decent interface, and the ability to store videos, pics, games, and movies/tv shows in addition to music. I like it because it holds ALL my music (483 cds), and I can pull it out and play games or watch downloaded tv shows when I get bored. However, the downside is the ipod classic does not sound as good as some of the other mp3 players (like my Zen Micro). I’ve compared the same mp3’s with the same headphones on both of my players, and the Zen Micro sounds noticably better. So you might not want to go with an ipod, or you might want to find people you know with ipods and ask them for a listen. I’ve heard the smaller ipods (particularily the nano) sound better than the classic. Since music is so subjective, I’d recommend you try anything before you buy it. Check amazon.com customer reviews on anything you’re considering, they’re surprisingly informative (but don’t buy from them they’re too expensive :rolleyes:).
Another thing to consider is, you can always just get a free mp3 ripper and rip all your cds to your computer. You can experiment with the sounds of different ripping methods and different free software players (i like winamp www.winamp.com) to listen to it on your computer. Once you get used to your collection going digital, you can shop around for a physical player. Or you can hook your computer up to your stereo and don’t buy a player at all, it will only cost a few bucks for cables.
And maybe an iPod is the best choice. But will it be carried about? Will it be hooked permanently to the stereo? Lots of things to consider, including terminal failure issues.
Seeing as how you are a technophobe, I will add this piece of advice:
if you go with the dominant music player in the industry (iPod / iTunes), you will be able to find a lot more people that might be able to help you with problems than if you go with another solution.
I stopped using my iPod because I coudn’t stand dealing with the horrible pile of steaming feces that is iTunes. That’s a reason right there.
I have a barely-used, white Creative Zen Nomad Zen Xtra, 40GB, that I am willing to sell on the cheap. I don’t ever end up using it because it’s too bulky for my pockets (girl jeans have small pockets) and I never wear belts, so belt clips are useless. One of these days I’ll get one of those little skinny ones and start listening to mp3s on the go again, but until then the thing is just sitting here. Let me know if you’re interested.
There are plenty of iTunes alternatives available, if you really feel that strongly about some feature it is missing.
OpalCat, WinAmp will work with your iPod, if it’s not broken. Can I help you with it? (Alternately, if you don’t want it… 
)
My son inherited my iPod years ago. You wouldn’t want it anyway–it’s ridiculously old.
Absolute, I have issues with Apple’s general philosophy anyway, and prefer not to buy their products. Why would I buy an iPod and try to find another program that works with it when there are so many other players that are, IMO, better?
If you don’t like iPods to begin with, then there’s no reason. Some people like the iPod but complain about iTunes.
Check out RockBox. It’s a whole new operating system for iPods. I just tried out RockBox 3.0 on my 40GB iPod and am very impressed.
One of the advantages of RockBox is it will just play whatever music you copy to your iPod, no need for iTunes or any other special software.
The iTunes software is free. You could always download it, install it on your PC and rip a couple of CDs onto your computer. This way you can see if it’s something you can deal with without committing to any player. You can also hook your headset directly to your computer and evaluate for yourself if the quality is an issue. Personally, a 192 kps MP3 rip is suitable for my ears and the MP3 format is ubiquitous. If you determine that iTunes is not for you, you could always move your newly created MP3s into the software of your choice without re-ripping your CDs.
At a minimum you could then burn a new copy of your CDs if disk degradation is your main problem.
Going to chime in and say that the apple product, while more expensive is widely regarded as the most luddite friendly option. There is a reason why they have the market share they have. They are putting out a good product.
Well, as I said, I no longer have an iPod and wouldn’t buy another.