Hope you’re all enjoying OlliOlli2: Welcome to Olliwood on PS4 (or PS Vita)!
However, there’s a known issue when using Cross-Save for the First Time on either device. This will be patched. Have no fear, though - there’s an easy fix!
When using attempting to Cross-Save for the first time, first hit Reset Cross-Save before hitting Sync. Then simply Cross-Save like normal and you should be all good!
Enjoy skating through Olliwood, dudes!