Haha yeah same! I think adding this as a factor into Edwin's items will make things fun and slightly unpredictable. If he makes an attack it could go either way; same with just walking through a door or trying to ask a girl out. Sometimes it's funnier if a simple task like that fails.
That could be fun. Not all attacks go as planned, but some are pleasant, and some are not We had a chaos mage in my last DND party that rolled to see if her chaos magic hit, and it's done some awesome things, but it also killed my character a good 3 times directly or indirectly XD