Alternatives to iTunes (Mavericks/iOS 8)

Question

I recently "upgraded" from an iPod Touch 4 32GB to an iPod Touch 5 16GB, mainly because I wanted to see how iOS 8 works. I am syncing this with iTunes on a Macbook Air, but my music library is over 16GB. I have used a playlist to limit what music should sync, but it is still a significant amount of data, leaving almost no room for apps or other data.
I know that I can reduce the music data by creating a playlist that excludes specific songs, albums, or artists, but with this many songs in my library, it isn't worth my time to go through the playlist line by line. So I was wondering if there are any alternatives to iTunes that include a feature that would allow you to limit how much music data is synced to the device, and the software would randomly select songs from a specific playlist to fit that data limit. Older versions of MediaMonkey for Windows would do this, and I'm actually surprised that iTunes does not include this feature. This feature would allow me to set up a playlist of the music I want to listen to, and synchronize a random subset from the playlist up to a specified limit. Each time I perform a sync, the playlist would include a new, randomized subset, so that I don't have to completely exclude songs or albums from future syncs.

Answer 1

I am not aware of any such app. There are computer apps that can transfer music to an iPod but they are really manual.
Have you tried compressing the music so it takes less space on the iPod ?
To compress go to the Summary pane for the iPod in iTunes and under Options check the box that says "Convert higher bitrate songs to XX kb/sec ACC".  XX of 128 is a good compromise music quality and storage space.