Not to go all AxeMe on you, but seriously.

iTunes and the iPod were designed to work together seamlessly, and it sounds like you want some seams, so you're always going to be rubbing iTunes' fur in the wrong direction, and it's going to snarl at you.

You need to tell iTunes (or whatever program) to let you manually update your iPod, and then you can put on/delete whatever you want without it automagically updating/removing songs.

yup...it's in preferences. make sure manually update is selected...i did the same thing when i first got mine--i think apple thinks people want it to be automatic.

You can also use ephpod for synchronizing, instead of iTunes.

Speaking of which, where does "compilations" show up? I've looked through my iPod menus, but I can't see any "compilation" anywhere.

And, regarding your problem:

I made a playlist in iTunes of songs that my son likes. When I updated my iPod with the playlist, all of the songs I had on the iPod previously were taken off, and now only the playlist is on there.

That has never happened to me. I'm not sure I follow...How many computers, how many iPods, and how many iTunes are we talking about? If you've got an iPod on your computer, you can make as many playlists as you want without losing anything...The only problems I know of are when trying to synchronize one iPod with more than one computer (or perhaps more than one iPod on one computer), in which case manual update should work fine for you.

Capn, so I'm lazy today. Sue me.

I'm reading thru the user manual again, but papercake, amberglow, and bugbread answered all of my questions. Thanks guys ;)

I think my main problem right now is in my head. I have a crappy computer at home, and iTunes really hangs it up, to the point where I can't do anything else. It has so much needless shit on it. I guess I just need to get used to it.

iconomy, as to what compilations are, is that appearing in the browse sub-menu or in the main menu? Because that term refers, I think, to certain CDs, based on how itunes categorizes them when you rip them according to CDDB information. Usually best-of CDs get treated as such.

Ah, found the bit about compilations: It doesn't appear on iPod software 1.0 (which is what's on my iPod photo), but was added in either iPod 1.1 or 1.2 (I need to update my firmware).

And, yes, a compilation is like a various artists compilation. For example, a "Best of the 80's" album would have multiple artists, but part of the same album.

it is a resource hog.

there was an askme about alternatives--maybe try them?

Sorry, I shouldn't post before coffee, 'specially on a weekend.

Wow. That sounds like the answer to my prayers! I really miss my good old drag - and - drop Winamp, and hate iTunes so much. Thanks, amberglow! I didn't know there were others who disliked iTunes - everyone's always going on about how fabulous it is.

About the compilations - yep, it appears on my main menu - it goes like this

Photos
Artists
Compilations
Extras
Settings
Shuffle Songs
Backlight

I guess I don't understand how to get songs in there - in the compilations. I swear to you all that I RTFM ;) I'm guessing it's sort of like a playlist. I'll look it up again. I think I'm just bummed about what a pain in the arse iTunes it, and how nice and sweet and easy Winamp was, and why can't I have what I want when I want it. I promise this is just a mood I'm in right now and I will get over it and soon return to my usual happy-go-lucky self. But right now I freaking hate iTunes and I hate my iPod.

I'm going to try the Winamp plugin right now. Thanks again for the help, everyone.

I just uninstalled iTunes. The Winamp plug-in kicks the llama's ass. I'm way too happy about this!