Not sure what's going on but here are some things to consider: Was the sheet created with Charactermancer originally? If not, it might be lacking some needed CM flags. Are you running any third party extensions that might interfere with Roll20's normal operation? Have you tried leveling to 2 and then to 3? What you are doing should work, but it's worth a try. If all else fails, try just recreating the character. There's not that much data on a level 1 rogue that would make this too onerous.