A lot of conventions have been put on. There's a mountain range of Oral Tradition among the veterans ("SMoFs", though the word is used in other ways too).
The last thing you need is to spend money and energy on a problem which is solved, or relearning skills (like hotel negotiation) which we have masters of.
Last I knew, though it's been a while, there was a SMoFs listserv, with a lot of good people on it. Please start networking with the people who already know how to do what you want to do.
I'm not trying to tell you how to do your con, but there are mechanical considerations which are the same for everyone. How do you budget for your hoped-for number of people when you don't know if 20% or 80% will join at the door, after you've already spent most of what you have to spend? You probably want to set up a 501-c(3) to be the official sponsor to limit liability.
(Frankly, I'm not sure how self-conscious to be. I may be old enough to be grandfather of one of your target demographic, but I've been to a lot of cons, too, and have seen remarkable things. (A personal favorite is the Worldcon where someone said, "It's raining in the Art Show."
(Seriously, I want you to have the best shot of getting this done that you can. And Reinventing the Wheel can be way too expensive.)