not enough room to copy requested files

You don't have to "delete" songs, but instead simply remove some from the iPod so that there is enough room to add the new songs. If you have the option to Sync only ticked sings and videos turned on (checked) in iTunes, then yes, unticking them will cause them to be removed from the iPod, but keep them in your iTunes Library, ready to go back on when you want them.

An option that you might wish to consider is using Smart Playlists to mange your iPod. By creating Smart Playlists, in iTunes, that automatically remove and add songs to your iPod (acording to the rules you choose) it is possible to remove songs from the iPod that you can live without for a while and add new music in its place.

If that sounds like something you would like to try, but you need help in creating Smart Playlists, plesae ask.

KelcyBl wrote:

Is there a way to get more memory?

No. (Or rather, only by buying a larger capacity iPod.)

See the screen shot below:

1. switch to the Playlists view
2. click on the + icon at the bottom of the window
3. select New Smart Playlist

and this appears:

• Change the "Artist" drop-down to Playlist. The rest of the line will automatically complete as is Music. (So the line now reads as Playlist is Music.) Leave that as it is.
• Click on the + icon at the end of the line to create a new line for an additional rule.

• On this new line, change "Artist" to Last Played
• (As you change boxes, some of the other boxes will change what is in them. For example, the box at the top has changed from "Match the following rule" to "Match all of the following rules". Leave that as it is.) The next step here only appears when you select the Last Played option
• Change the second drop-down on this new line from "is" to is not in the last
• Change the box with the "1" in it to (for example) 5. You can change this later if you wish, see below
• Change the "days" box to Months
• Select the Match only ticked items box (so that the tick is displayed (on)

You should now have this:

click on OK

... notice the highlighted Playlist 2 text? (If it isn't highlighted, simply double-click on it.) Overtype it with your choice of name for your Playlist and tap your enter key (on your keyboard). The Playlist is listed on the left. Notice also, the size of the Playlist in the status bar at the bottom of the window. If it isn't displayed, use the CTRL and / keys to turn it on.

That's it!

If the Playlist is still too large for your iPod, simply revise the Playlist, by right-clicking the Playlist (in the left panel) and selecting Edit Smart Playlist. Change the 5 (months) to 8 (months) and watch what happens:

the playlist was 106GB, but now becomes...

• When Syncing your iPod, change the Sync options to Sync Selected Playlists and choose the KelcyBl Playlist.
• On the iPod, you can still choose whichever songs you want (from the ones on the iPod) by using Artists, Albums, Songs, Genres as you did before. The playlist simply controls how much is on the iPod. (You can use the playlist as a "play" option.)
• When you next Sync your iPod with your iTunes Library, iTunes will remove from that Playlist, any song that has now been played. It will have put back any song that was last played before your chosen time (5 months, 8 months or whatever.) This revised list will then be on the iPod.
• You now have an automatically updating list of songs, small enough to fit on your iPod but without songs you have played in the last 5 months.
• BUT WAIT - you say... there are songs I want on my iPod all the time, even if I have recently played them. Also, I want to have those recently played songs on the iPod in case I want to listen to them again. No problem.
• If you have space, and wish to do so, you can select additional playlists, for example the Recently Played playlist. By default, this playlist is set to two weeks. This means that once you play a song, it is removed from the KelcyBl Playlist, but added to the Recently Played playlist, where it will stay for two weeks. then it is also removed from the Recently Played Playlist as well.
• By Syncing the Recently Played playlist to your iPod as well, a song will be on your iPod if it hasn't been played for five months, or if it has been played in the previous two weeks. But, if it was last played more than two weeks ago, and within the last five months, it will not be on your iPod, thereby reducing the space required on the iPod.
• If you have songs that you always want to be on the iPod, for example, songs that you have rated as five stars, simply create a Smart Playlist of songs rated five stars and Sync that to the iPod as well.
• You only have to adjust the numbers to keep the total amount of music on the iPod within its limits and the work will be done for you.

That means that there is not enough space on your device, not on your computer. Try making space for your newer music.

.

reply will follow in a few minutes

I realise that's a long post. But if you try it, then by adjusting the various options in the playlist, I think you will find it will do the job

Any questions, please ask