It should not be that big of a problem. You should be able to put 2000 song on an iPod / iPhone with 10/15Gb of free space. Check your free space on your devices.
You can try and convert your songs to 128 kbps, you can do this on your device under options (scroll down it's under the back-up). This will save a lot of room, 320 kbps songs takes up a lot of space.
If that doesn't work, try making a song list with all you're favorite songs and put them on you're iPod / iPad