Some songs not transferring over to new computer

Some of my music will not transfer over to a new laptop. Some of the songs were purchased or downloaded 5 years ago when I had a different apple ID account and different laptop. All computers have been "authorized" (I have 4 out of 5 authorized) but whenever I sync, about 50 or so songs will not transfer over. I try syncing and transferring purchases but nothing works.

Any ideas?