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"Let's be serious here. The BF may be something of a jerk, but his concerns are not "nuts." "
Fine. Let's be honest here, too. The primary issue is NOT that the boyfriend has concerns about her past. The issue is that he appears to have made a conscious choice: rather than break up with her over his concerns, rather than make an honest attempt to deal openly and honestly with the issue - which she has explicitly asked him to do - he has rejected all possible solutions and chosen instead to torment his GF over her past, a choice that satisfies nothing except his own sense of moral superiority.
The issue is not that he's judgmental; it's that he's a mean asshole.