I had a spat I described in one of my blogs with an Apple Support analyst some time back; I remember I had stumbled across some puzzling interface anomaly and pointed out that I've written articles and book chapters on software usability; I wanted her to forward my comments to relevant Apple developers/managers. She responded with a skeptical tone and all the enthusiasm of not-invented-here syndrome that there were Internet pages or forums to post complaints or suggestions.
When I moved to West Virginia from Maryland at the beginning of 2014, I had run into an issue with my second iPod shuffle. WalMart online had indicated that they had new Shuffles for sale at my local Wal-Mart, but I couldn't find them on display; during my hunt I found a different mp3 player with more capacity but a third of the cost. I guess I shouldn't have been surprised that unlike the Shuffle, the iTunes software didn't interface with the new player; the practical issue was that while it was fairly easy to refill my Shuffle with updated playlists, sifting through hundreds of music tracks to copy and paste them to the new player was a nontrivial task. But I discovered when I installed the Media Monkey player and read in my Music folder, it had somehow imported my iTunes playlists. I could then select all the songs in the chosen playlist and write them to the mp3 player. (I think I wrote this in one of my my flagship political blog daily (miscellany) posts; I didn't think the workaround was substantive enough to write up in this blog.)
However, I had merely deferred the playlist functionality issue. I did realize that iTunes library file (iTunes Library.itl) was critical because in the past I had to deal with corrupted files in starting up iTunes. But for the most part I had blackboxed the library files--until yesterday, when I had finally caught up on my podcasts and decided to launch one of my playlists--only to discover that the handful of playlists were gone. In essence, I was back to the problem with the mp3 player--I didn't want to sift through hundreds of mp3 tracks to rebuild my playlists. I stumbled across this Apple Support note, which basically tells you to exit iTunes (if necessary), rename/archive the existing itl file and copy/rename the latest time-stamped archive file from the "Previous iTunes Library" folder. To my relief, I was able to find my playlists in that last archive file and didn't have to iterate up the list of archives.
But this wasn't the optimal solution either: I had made a number of changes to my music files, podcasts, etc., since that snapshot library file. The right click menu seemed to be an incoherent blend of structural (edit/delete/clone/burn playlist) and functional (play/shuffle/skip playlist tracks) items. Now from my reference, I wanted to apply my preexisting template/advance organizers, e.g., the file menu, i.e., open/import or save/export playlists. It turns out that there are options to import/export playlists--but you have to navigate through File/Library menu (which I think is unintuitive). The export functionality requires you to first select the target playlist.
So I exported my handful of playlists (with a playlist.txt names), exited iTunes, reverted the library filenames, and brought up iTunes. I then imported the playlists through File/Library; I got warnings about missing music files, which in my case had to do with my Amazon music folders somehow not being registered with iTunes, the simple solution being to add the Amazon folder to the library through the file menu. (Kudos to the wonderful Voidtools' everything freeware utility.)
I've now made a note to synchronize my iTunes itl and playlist export files with my cloud-based storage accounts and my daily backups to external drives.
