Strange behavior when playing certain tracks

Ok, this is odd. I've had this iPod for a few years now, it's never given me any problems at all. I have been using/syncing it with a PC laptop, using iTunes for PC. Well, I bought a MacBook finally, and knew better than to try to sync it with the Mac, but I downloaded some tracks and moved them to the PC using a flash drive, then imported them into iTunes, which I would have thought should change any PC/Mac formatting discrepancies/issues, but perhaps not, because now the iPod sometimes will skip for a few seconds and then crash and go back out to the list of tracks (these are in a playlist) when starting to play a track. But if I then reload that track it will almost always play it fine, if not immediately if I keep trying it will play it. But then maybe the next track or the one after, it will do the same thing. I have them on shuffle but it does it regardless. Now, I bought a few more tracks, this time downloading them directly to the PC, and importing them on that iTunes and syncing the iPod as usual on the PC (remember I never have synced it with the Mac) and it's now doing it with those tracks as well, basically everything in that playlist, and one other playlist containing those tracks. Does not seem to do it on any other songs/playlists, and all these tracks play fine on either computer and also the Pioneer Rekordbox DJ software/controller that I have. What do you think? Am I going to really have to wipe it and reload everything? This is 64 gigs of music I've bought over several years, plus a good bit from Bandcamp as well, so that is a major, major undertaking. Thank you