Who should be best man and bridesmaids?

It's your guys big day and I say it should go how you two want it to go. If it's really important to him to have them both be his best man, and is also OK with you, then do it. I really don't see it being a big deal, and if some people think it's strange who cares. It's your wedding day not their. As for the stag party, you said one is really responsible, so if they both have to plan the party together than I'm sure he'll make sure the other one doesn't go too crazy. Plus it's not about trusting the best man, it's about trusting your husband no matter what situation he's put into. Hope that helped and congratulations.