Jeeze, man, take a couple of deep breaths. You seem really stressed out. This should be (mostly) fun! If you’re this anxious two years out, you’re probably taking things too seriously. You have two things to be happy about: a) you’re marrying the woman you love; b) you get to have a fun party with all your friends and family. In what way will pointless stress and anxiety make either of these things more enjoyable or meaningful?
A couple of things to keep in mind:
1) This is ONE DAY. You do not have to find a way to weave your dorky interests into the celebration (and I mean that kindly–I happen to be in grad school for history). Everyone coming to the wedding knows who you are and loves you for it. It’s not necessary to remind them that you’re a history buff by putting little figurines on the cake. Sure, your wedding should reflect who you are. So should your apartment. I trust you don’t consider custom-made Roman Empire themed shower curtains a necessity.
2) It is totally okay not to be into every little detail. I’m not sure why there’s no gray area between perfectly even division of labor and your Fiance doing everything. Of course she’s more into flowers and centerpieces and colors and bridesmaid dresses than you. Why not think about the things that actually do matter to you, and just reserve veto power/help pick between her favorite 2 options on the rest? In the long run, I think you both will feel much happier and less frustrated with each other if she isn’t trying to get your opinion on every.single.little.thing and you aren’t feeling guilty about not giving a damn.
Okay, on to your questions:
1) My Fiance and I couldn’t pick between friends, so we don’t have a best man/maid of honor. It’s worked out wonderfully for us so far. But we are having a pretty small, laid back wedding, so it’s not like there’s a whole lot for them to do. Still, it might be something to think about. Your best friend could stand closest to you and hold the rings; one of your other groomsmen who’s more confident speaking in public could give the toast (maybe they could even write it together and he could speak on behalf of all the groomsmen?); your brothers could help you with logistics (choosing a recommended hotel for your out of town guests; organzing a family brunch; whatever needs doing). IMO, having a wedding that reflects the people involved is about this kind of stuff. Do what makes sense for you, and be flexible.
In terms of your best friend and anxiety about the bach party, just tell him, clearly and firmly, that if he hires strippers/tries to take you to a club, you will leave. Party over. None of this instructing another friend to rescue you nonsense. What is that about? You’re not capable of walking out the door and calling a cab? Anyway, if you’re clear about your wants and expectations, I’m sure your friend will do his best to make sure that you have the kind of night you want. As an alternative, if you’re not into the crazy partying/drinking thing anyway (and good for you!) you could do a Jack and Jill type thing, at least for part of the evening. Say, meet the girls for dinner, and then go out for drinks with just the guys afterwards. That way if your brothers aren’t into extended festivities they can peace out after dinner.
2) I guess I already kind of covered that.
3) I’m sorry, that sucks. Maybe use some humor? Also, your Fiance should be aware of this and on your side. Ideally, she should speak up: “Actually, Grixis asked the question, and I think it’s a good one. What do you think about that answer, sweetheart?” or “Honey, why don’t you start with the questions. I know how important X is to you.” My guess is that vendors are used to the brides being totally on top of the planning, and the dudes just tagging along to be good sports. It’ll take some conscious effort on her part as well as yours to make sure that you’re included. Let her know how much this bugs you and see if she steps up, or if she just goes along with them ignoring you.