I need to put a callout for speakers. I've reached out to a few personalities on the board, but hoping for others. I f you are interested in attending this and feel like you could contribute content in the form of a 60-90 minute (or so) presentation, let me know. Please pass the message around. PM me with a speaking outline if you feel like you can contribute.
I always enjoy the more open discussion/round table/socratic seminar than a "presentation" per se, personally.
Right now I am working on the premise that we have 8 speaking slots, 2 of which are keynotes. (one keynote speaker, plus 4 workshops per day. 2 workshops running consecutively.)
Running multiple simultaneously is a good idea. Camp Mustache always has 3 to choose from, so while sometimes you have to make a hard choice of what you'd rather learn about/discuss, there's always something for everyone, since they're quite diverse. Having one going, that you aren't interested in, is meh--at least two, like you mention, is good.
I don't think you need to line up too much of that too early. One or two main speakers early is fine, and the rest put out calls once signups are over for people who want to share. Mustachians are full of knowledge and awesomeness, so you'll likely find people with cool ideas to share/present.
I think the first CM they got Pete and JD Roth to commit, then just whinged the rest of the presentations by coming up with a list of topics, and assuming people would be interested in discussing them (I didn't even know I was "leading" the real estate discussion until the day before, while at the Camp). So I wouldn't worry too much about trying to get everything lined up perfect for the breakout sessions, IMO--that will all fall into place easily.
Food is a giant mystery at this point. Diets, preferences, and cooking facilities need to be accommodated and figured out.
So the first year, there was giant cooking facilities. The organizers brought in a bunch of food, and then a few of them, and their spouses, were stuck cooking the vast majority of the weekend. The food was delicious, but it was a bummer for those who had to spend so much time on that all the time. Cooking for 50+, and cleaning, and such, is no small feat. And while you think people could pitch in, there's only so much room in a kitchen, for both the cooking, and cleaning--washing dishes, for example, takes a long time, and there just isn't room to fit in a lot of people to do it, even if they're willing to help.
The second and third year, we went to an all inclusive camp. The staff there did all cooking, and cleaning. This obviously made everything more expensive (IIRC tickets went from roughly 200 or 250 to like 400 or 450), but made the experience way better/easier. No need to even worry about food at all.
Yes, the tickets then become pricey for some, but you'll still have enough people who want to go, and if you run it at cost, meaning people don't feel like you're making a profit off of them, they'll realize that $450 or whatever for 3 nights + 3 days of food isn't actually that bad.
And then you just show up, sit down at a random table with friends/new strangers, eat, enjoy, walk away, keep chatting, no need to ever worry about any of that stuff. Next meal, sit at a different table, introduce yourself to new people, and get to know them! I'm normally not a fan of all inclusive, but it made the weekend way better when they switched to that model.
One resort I am considering is offering a fleet of (ugh) kayaks for free use, a pontoon boat for rent, and a variety of soft activities (badminton, volleyball, etc.) Does this stuff matter? Or is sitting around a campfire enough?
Honestly, we spent so much time chatting, doing the breakout sessions, playing games, etc. that there wouldn't even be much time for these type of activities. You may go for short walks with people. They schedule one long hike each time that takes up the bulk of the 3rd day. The campfire (with smores!) each night is fun, for sure. But I wouldn't worry about a whole bunch of "extra" activities, because people who get up early and go downstairs (or to the central area, or whatever) suddenly have a bunch of interesting people to chat with, they're not going to go out on their own to kayak.
People go to the retreat to meet and hang out with other Mustachians, and while you can do that with other activities, you just... don't. Cause you're so busy hanging out. :)
Just my thoughts. :)