Yeah Zen had pretty horrible software, but it did its job pretty good anyways. One thing that really pissed me off about Zen was that I bought an expansion card when I ran out of the 8 gigs that it had (bought a 8 GB MicroSD, at least I think it was MicroSD, memory card, but it only worked like 30% of time and it was totally random when it'd work and when it wouldn't). Luckily digital camera used the same memory card type and was only 1 GB so the money wasn't wasted.

I got an Ipod now as well, and I like it much more, it's much easier and more intuitive to browse your music/playlists with an Ipod touch than it was with Zen, and I don't really hate ITunes that much either, and I never found it bothersome to sync my music. All you need to do is add all songs from your HDD (I just added my E:\Music) to the ITunes library. Then you check that "only sync checked songs" checkbox in sync options. Then you just check the songs you want to sync, and uncheck the ones you don't want to sync, and what makes this very easy is that you can use the browser to list all songs, or all songs by certain artist, or all songs of certain album etc. and you can then mass select/unselect checkboxes with ctrl+click, meaning that it's very easy to sync certain artist's music, or just one album etc.

I would love to sync my whole music folder, but 16 GB isn't nearly enough.

that's also a lie, my ipod mini from 2004 allows me to play mp3 and wav too so i would think that later models support the same formats or maybe more

Yeah, I'm pretty sure iTunes just doesn't allow .wma files, for obvious reasons.

Edit:

iTunes 8 can currently read, write, and convert between MP3, AIFF, WAV, MPEG-4, AAC, and Apple Lossless.

The Windows version of iTunes can automatically transcode DRM-free WMA (including version 9) files to other audio formats, but does not support playback of WMA files and will not transcode DRM protected WMA files.

the files on your ipod, i'm pretty sure are going to be AAC no matter what you do. When you import them into itunes, it converts them

the files on your ipod, i'm pretty sure are going to be AAC no matter what you do. When you import them into itunes, it converts them

No, they're not imported when you import them into iTunes. Some formats are converted, like WMA files, but MP3 files are not converted. Dunno about when they're transfered to iPod though, there might be a transparent conversion, but I somewhat doubt it!

you don't need to use itunes to load music and videos in your ipod anymore.  Winamp can read ipods now, it can play and rip songs off any ipod without erasing the whole thing.  So for example if you have alot of music in your ipod, you can delete the copies in the computer because you can always pull them out by using winamp.

besides, winamp uses less resources than itunes, so your pc will be more stable, and winamp has extra stuff that itunes does not.

But if you want a drag drop interface...

there are alternative firmwares to the ipod that you can use such as rockbox.
with rockbox you can turn your ipod into a drag and drop mp3 player so you don't need to use softwares like winamp or itunes to add/remove tracks.




Also I suggest you get an older generation ipod because, from what i know iTouches cannot be used as hard disk drives, which is one of the reasons why I like the older generations better.

Also I suggest you get an older generation ipod because, from what i know iTouches cannot be used as hard disk drives, which is one of the reasons why I like the older generations better.

There are a bunch of software that lets you transfer files between iPod Touch (and iPhone) and your computer.

There are a bunch of software that lets you transfer files between iPod Touch (and iPhone) and your computer.

You will only be limited on doing these file transfers between your itouch and a pc that has that software. It'd be easy if it was a patch that you load in your itouch that permanently lets you do it but no. 

The advantage of old generation ones is that its a plug and go hdd, you technically don't need to carry around thumb/flash drives when you have one because all computers will recognize it as a drive.  He can't just download the software whenever he wants to especially if he is on a public computer, or another one,  too much hassle.