Xbox Music Cloud Sync

So I have a desktop and Surface Pro, both now running Windows 8.1. As long as I've had my Surface, I have been unable to find a way to make the cloud syncing in Xbox Music actually work. I have 252 artists, and it only ever uploaded 154 of them to the cloud. Even then, it skipped a lot of songs in each album uploaded, as well as most artwork. What's the deal? There's no way to force uploads, or any way to troubleshoot. It's just a checkbox for uploading to the cloud, and that's that. Anybody else have this problem?