alright i figured it out. So the issue was that i had originally created these two characters in a campaign "Character Sandbox", and I imported them into Roll 20 Characters so i could move them to another game. They worked fine in the other game and synced perfectly. However, when I wanted to return them to their original game there was already a sheet for each character. I foolishly just moved the original character sheets to a different folder and added the characters back into "Character Sandbox" via the Roll 20 Characters "Transfer to Game" option. This resulted in the imported characters for some reason using the same values, settings, toggle states, from their original sheets and overwriting the imported character sheet's options. After rediscovering their old sheets I noticed the problem I was facing, one of them always rolling advantage even if I toggled it to normal, was reflected in the old sheet. I deleted the old character sheets, removed the imported sheets from the game via Roll 20 Characters and reimported them. They now work perfectly. TLDR; I added these sheets back into their original game and their old sheet's settings were overwriting their new ones. Just delete the old ones and re-add the characters into the game from Roll 20 Characters