I added a bunch of new music to iTunes lately (not bought from the store) and a bunch of songs started doing this weird thing where somewhere between 90 and 30 seconds from the end, the song would just skip to the next. Which was super aggravating. I tried deleting the songs and reimporting, which was the common fix I found online, no deal. Skipping problem persisted.
What I finally got to work was going in to the iTunes folder and deleting the iTunes Library.itl file. Open iTunes back up and it thinks there’s no music at all; then you just have to reimport the iTunes Music Library.xml file using the “Add to Library.” I backed up the xml file right before I did this just in case, but using the one already in the folder brought back all my music and playlists just fine. (Also preserved all the play counts, etc.) It just took a while to reimport everything. But now all the songs are playing their full length.
Just figured I’d mention this here in case any of you ever run into this problem. It took a stupid amount of time reading through forum threads before I found the one person who mentioned this fix. So now it’s in two locations!