Hello htmlmason,
Are you streaming these playlists or are they downloaded to your PC? We'd recommend downloading them to test it further: Add and download music in iTunes on PC - Apple Support
Download music to your computer
1. In the iTunes app
on your PC, choose Music from the pop-up menu at the top left, then click Library.

2. To download music in your iTunes library to your computer, do one of the following:
- Click the iCloud Download button
next to the item.
- Move the pointer over an item (such as a song or album), click the More button
, then choose Download.
To view only your downloaded items, click Downloaded in the sidebar on the left.
If you don’t renew your Apple Music subscription, downloaded items remain on your computer, but you can’t play them until you rejoin.
Note: Music you download from Apple Music to your computer can’t be burned to a disc or transferred manually to a device, such as iPhone, iPad, or iPod. Music can only be downloaded to a device directly from Apple Music. See Intro to syncing.
If this only happens with streamed content, then we'd recommend using these steps to try to solve it: Resolve issues between iCloud for Windows or iTunes and third-party security software - Apple Support
In case this persists, are you an Apple Music or iTunes Match member? As these steps may be different, if that's the case.
Hoping to hear back, take care.