Super Off Topic - Weddings

Hey all. I've been to three weddings in the past couple years that I've actually been old enough to care about who's getting married and I will be a groomsman in one for sure and maybe two this summer, and I am having a hard time figuring out what's appropriate.

The three people that I cared about enough to go to their weddings were an ex band mate, my half brother, and a good friend of mine from work back in the day. I wasn't in any of them, so it wasn't hard but now that I get to be in some I'm confused.

First off, the wedding I am going to be in. One of my best friends ever is Kelsey, and she's marrying a mutual friend of ours that shes been dating for like 5 years on July 25th. They are doing it on a budget, but it's still going to be a nice ceremony. I want to get them something nice for a gift, but I don't know how much to spend. For the other weddings I usually spent like $30-$40, but isn't it customary to spend more being in the wedding party? Next question on this one is the bachelor/bachelorette party. See, the maid of honor and best man haven't made any moves on this, and I think Kelsey and her fiance want to get the ball rolling on it. They have some ideas of their own that they'd like to do, but I think they are kind of afraid to ask them about it, and they asked me to bring it up. Is this out of my place to suggest some things? Or should I just say "Hey, what's the deal?" or is even that too much?

I've got another problem with my best friend from high school and his marriage, but I need to word that properly. I'll get back to ya'll on that.

it shouldn't matter how much you spend on the present dude.

I would say just get thiem something you think theyll like. Im getting one my good friends like a gag gift and a gift certificate to one of the nicer restaurants in town so in total like 60-70 bucks but of theres something out there that you think they would really like i dont think $100 is unreasonable for a really good friend.