I'm considering buying an iPod classic 160GB... ?

I suggest you buy that iPod. I have to uncheck quite a lot of songs to fit in my 120GB iPod because I’ve got 151GB of music on my laptot :) I love having all those songs in my pocket!

Maybe I’m biased as an apple fanboy, but I love the iPod. I have a 5th generation iPod nano, and after comparing it to several conventional mp3 players, it’s simply a much better product. The software is head and shoulders above anything else I’ve seen. Buy it.

I have an iPod classic, because, like you, I need a lot of storage. I like it a lot. I’m a PC gal, but I’ve only used iTunes to manage my music, and I’ve only used iPods as mp3/4 players. They’ve never given me any reason to think they would “ruin” my computer…

The playlist options that you list are all there; you can drag and drop songs (single or multiple) to playlists. It’s all pretty easy to manage. The headaches I have experienced are: (1) it seems like every month, there’s a new version of iTunes that they want you to install. There’s an option for “don’t ask me again” which might work until the next update. (2) Maybe this has been fixed in a later version of either iTunes or Adobe Photoshop or both, but if I have both programs open at the same time, my iTunes library is erased, which means I have to rebuild it (this is time consuming). (3) It can be tricky to move your iTunes library from place to place… you probably want to decide where to keep it (i.e. which external hard drive if you’re using one) before you put all of your music files in there. I would recommend experimenting a little with a few tunes in it, so you don’t tear your hair out while you’re learning how it manages music.

Overall, I like it (even though I’m no Apple fan) – it’s free, and it works well, and it does all I need it to.

There are MP3 players with large capacity other than iPod and Zune. For examples:

http://www.epinions.com/prices/MemoryKick_MediaCenter_120_GB_MP3_Player
http://www.epinions.com/reviews/Archos_AV4100_100GB_POCKET_VIDEO_REC_Sound_Card

I have installed iTunes on Windows 7 and it doesn’t seem to have done any harm.

Hmm there are also these tablets at 250GB and 500GB:

http://www.amazon.com/Archos-70-Internet-Tablet-Black/dp/B00422XOEG/ref=pd_sim_sbs_e_1
http://www.amazon.com/Archos-501598-500-Internet-Tablet/dp/B004LLQ47M/ref=pd_sim_sbs_e_1

Haven’t read through the thread. I have one and like it. It’s easy to use. You have to use itunes with it though. I like itunes, though.

@Zyx: “Has anyone figured out how to use an iPod without iTunes yet?”

Not to my knowledge. And if you’ve had the pleasure of being able to just treat your mp3 player (or Android phone) as a drive, being forced to use iTunes is unacceptable.

That said, the iPod classic might be your best bet for large storage of mp3s.

Have you considered some of the cloud storage options, like Google Music that you could use with an Android wifi-enabled mp3 player? Just a thought.

There have been, and probably still are, some marginal competitors to Apple and the iPod. For example, SanDisk makes and still markets the Sansa mp3 player, but the biggest one that I’ve seen advertised (on the SanDisk page) was only 16 GB.

So if I were you (and in one sense I am), I would go for the ‘classic’ iPod – and use CopyTunes to manage the thing. You don’t need iTunes. I wish that I had my classic iPod back, because that used to play and charge simultaneously when I had it connected to the car stereo. The newer models, for some reason, won’t charge while they play. I hate that. To whoever stole my iPod classic: I’ll trade you my iPod Touch for it, straight up.