iTunes software sucks. It is one of the most user unfriendly POS programs out there. I think I mastered Adobe Photoshop quicker than the iTunes.
In any case, I set the iTunes preference to Manual updates. This way I don't keep all the junk on my PC and whatever I upload I delete afterwards from the hard drive. The manual setting is the only way(I think) to delete songs from iPod. But be careful when you change from automatic update setting to fully manual. It may refresh your iPod. Also, do a google search on ipod programs. I think there may be free versions of non-apple software that may have better features and is more user friendly.
In any case, I set the iTunes preference to Manual updates. This way I don't keep all the junk on my PC and whatever I upload I delete afterwards from the hard drive. The manual setting is the only way(I think) to delete songs from iPod. But be careful when you change from automatic update setting to fully manual. It may refresh your iPod. Also, do a google search on ipod programs. I think there may be free versions of non-apple software that may have better features and is more user friendly.