iTunes is a resource hog, which it is. But I can still surf the web, edit pictures, and back up my DVDs while iTunes is running. I do, however, have 4GB RAM and running 64bit Vista so that might have something to do with it.
iTunes likes to organize things the way it wants to. True, but you can kind of organize it your way. But after moving my library to two different laptops, I decided to let iTunes do the organizing for me. Made it easier to transfer library to new laptop and have my iPods think they're still on the same computer.
Commenting on the fihart's post about his friend not being able to find the stuff he's ripped on iTunes: Really? The default setting is to put music in the "My Music" folder. Within that folder is another folder called "iTunes", then "iTunes Music." Or if you can see the songs within the iTunes application, right click on the song and select "get info." On the bottom of the first tab, "summary" page, will be the path where the song is located.
iPods are married to one iTunes library. Try auto syncing it to another one and you can lose your content. There are some hacks to get around this. You can also do a manual sync and just do the drag and drop thing within iTunes, but I like autosyncing.
You might want to try iTunes. If you love/like it or hate it that will give you your decision about whether or not to get it. It also may help to try one out. My best friend and her family played with mine over Christmas...she ended up buying one for herself and her 9 year old daughter(who maintains her own iTunes library). Her husband is probably going to be getting one shortly. He keeps borrowing hers.
Whatever you do, stay away from iPod Touch/iPhone wannabes. What I mean is the look alike knockoffs. Yeah, that one was extremely expensive and it's only 4GB. Camera probably sucks. And that picture screams, "cheap." And touch screen? Looks like you have to use a stylus (which may be a bonus for some). You can buy a 32GB Touch for that kind of money. I've seen knockoffs that are a lot cheaper. Don't do it!
I've lived with iTunes for 5 years and I've had no problems with it. I loved my 1st gen Touch, so when 2nd gen came out I bought one too. I also own a bunch of other players (a couple of Sonys, Creative Zen V plus, SanDisk Sansa Clips). I keep coming back to my Touches. I carry them with me everywhere.
But iPod/iTunes isn't for everyone. That's why you should try iTunes before getting anything.