Thanks for the replies everyone. I've been trying to gather info on filename length restrictions ever since I ran into it on my Win XP system (NTFS) the other day. Gave me quite a scare because I couldn't play, rename, cut, or delete one of my MP3 files without getting an access denied error (or something along those lines). My first thought was that maybe my hard drive was breaking down. Luckily moving the folder that contained the file fixed the problem.
My file naming scheme involves either "Genre\Artist\Date - Album\Artist - Track - Title.mp3" for most music, or "Genre\Album\Album - Track - Title.mp3" if it's a soundtrack. As you can guess and I've recently discovered, this can result in some spectacularly long filenames. From what I've been able to gather, FAT32 and NTFS file systems are limited to 255 characters, and this includes the whole directory path and not just the name of the file. At least, that how I understand it to be anyways. iRiver uses FAT32, so I think I have that all squared away if I'm correct.
Regarding the iPod, as near as I can tell iTunes automatically renames files (on my PC too or only when copying files to the iPod, I don't know yet) and builds a playlist from the tags. Is that correct? If so, what happens if a file has no tags? Yeah, I know what your thinking. I could probably just download the software and figure it out for myself. But I still haven't decided which unit to buy yet, and I'm a little afraid of what iTunes might do to my files if I'm not careful. Nevertheless, I am leaning towards the iPod because of a few well thought out accessories (like the Monster all in one FM tuner 12v power cable for example), and easy charging abilities (from USB/1394). Plus you can get an inscription free if ordered before the end of September which is great since this is going to be a gift.
Anyways, thanks again for the replies. Hopefully I'll be able to have everything set up and running smoothly right out of the box for her, which ever unit I choose to get. Hehe, and it's not just the player that is going to be a surprise to her, but also the massive collection I'm gathering/encoding/sorting and getting all tagged correctly so that they work properly with all the players functions. Can't wait to see her face when I explain what 40GB of music actually amounts to, lol. Take care all!