I would see it as a good thing too, provided, as you stated, that the former bully doesn't influence your son in a negative way. And, definitely be on the lookout for #2's return because he may feel threatened by your son's friendship with #1. Ugghhh.... it's tough huh!!!!!
That social skills class sounds really neat. We too have been facing some social issues, which have been greatly helped by the fact that I now send four extra little airheads for snack. I constantly question whether I am teaching my girl bribery, though, we do openly talk about how she should never have to "buy" someone's friendship.