Can't get new music from iTunes to iPod

I currently have an iPod Touch.  Have downloaded the most current iTunes.  Have the latest software update for the iPod.  For numbers sake, I have 75 songs on the computer iTunes, 300 on the iPod.  Want to get music and playlists from iTunes onto iPod.  Have repeatedly tried syncing to no avail.  I don't want to erase everything off the iPod in order to do so.  Likewise, how the heck do I get the extra 225 songs from the iPod onto my iTunes??  All of the trouble started when I 1) added an iPhone into the mix and had multiple devices involved and 2) did the most recent iTunes update (which I HATE!!!!)
So how the heck do I do this??  I do not have a 7 year old in the household to tell me how to do this. 

Transferring tracks from an iPod back to iTunes has been covered here a number of times already, but again:
First, you need to prevent automatic synchronzation with a blank copy of iTunes. While connecting the iPod to the computer, hold down the Shift and Ctrl keys in Windows. This should stop the iPod from auto synching with iTunes and the iPod will appear in the source list. Wait until you are sure the iPod has mounted, and that it will not auto sync and then you can let the keys go. This may take between 3 and 25 seconds depending on your computer.
Then if you're using iTunes 7, you can then copy music that you purchased from the iTunes Store back to iTunes directly (use the Transfer Purchases From iPod command under the iTunes File menu).
If you're not using iTunes 7 or want to copy back other tracks, the easiest way will be to search VersionTracker for "iPod". You'll find a number of utilities that can transfer your tracks and your playlists from your iPod back to your PC.
It's also possible to do this manually, but the procedure is rather involved. If you're interested, though, see this thread:
MacMuse: Computer crashed
Hope this helps.

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