I have an iPod Classic 5.5 Gen and I was wondering if there’s a way to just drag and drop music without iTunes and just using something like a Chromebook. Is that possible?
If you use your friend's laptop, you will want to use your own library signed in with your Apple ID and your music. Using his Apple ID and his music will erase the iPod of those tracks if you ever sync with your own library again.
Manual management will enable the drag and drop. The tracks will need to be in iTunes (your library, on a USB drive for example). Hold SHIFT and start iTunes, then select the library on your drive to access your music.