iTunes 12.2.2 iPod classic will only sync once without reboot

I am a holdout that loves my iPod classic 160gb. Especially since Apple refuses to fix the music player on the iPhone to correctly deal with live updating playlists (but that's for another topic).

I've been having a lot of problems recently syncing my iPod classic which makes me worried that Apple is no longer really testing iTunes with the classic now that they don't sell them. Ever since I updated to 12.2.2 I am having a wierd issue. I can usually get iTunes to recognize and sync my iPod the first time I connect it. But after that, if I try to sync again it says the device cannot be found and can't be synced. It is very strange.

I have to reboot my laptop completely and restart iTunes in order to get it to sync my iPod again. This is really annoying especially since I can't add new playlists to the iPod can can't have my iPod reflect changes or songs played while I'm on my laptop without the reboot,

Has anyone else seen this issue?