I've been to Gencon and Origins for the last couple of years, but I am only certain that I can go to Origins this year. I'll try to go through your issues one by one.
1) I believe next year will be big for Starship Troopers when EVO comes out. I know that Mongoose does demos in the vendor hall or in the minis halls if they have the tables available. My first Origins was spend doing demos of SST and ACTA in the minis hall. We had a LOT more demonstrators come to the big cons then. Hopefully this year we'll get more recruits
2) There are a lot more games to try than just Mongoose's. I have a friend who goes to the big cons just to roam the vendor hall and try new games. He came home with a huge bag of free stuff from Gencon. I did get him into a few paid events using generic tickets, and he had a blast. My wife is going with me to Origins this year for the first time and I'm sure she's going to find games that she likes that I've overlooked in the past. This is a much better place to "shop" games than many of the FLGSs because many of the creators are there to show how the games are played.
3. I think more stuff will open up closer to convention time. I'd keep checking back. Some of the more pricey seminars actually have supplies and projects. They could also be seminars by people who do them for a living. I'd hate to see how much a Bill Clinton talk would be.
4. I don't know how to help you there. I wanted to play a particular game one gencon, signed up for the only game being run. Showed up at 8am and was there with a full table of players. The GM never showed. In that case I'd have rathered it not be listed. I ended up playing a non-d20 homebrew game that rocked.
I'm not sure how you got $80-100 for events, but I won't argue. I know True Dungeon's not cheap and a big pull and I'm sure there are others.
Travel expenses are what may keep me from Gencon. I have a free room for the con, but gas and food aren't going to be cheap. Plus I'm not taking my wife to this one. Luckily I'm close enough that I don't have to fly.
One place where I get a break is that I'm a demonstrator so my badge is paid for by Mongoose in exchange for me demonstrating their games. Also I usually get together with a group so we cut our room expenses. Rather than 2 people paying $100 a night, we get 6 guys together paying 15 or so a night each. Then find someone to carpool and cut the expenses there.
Will what I say make it work the large expense? I don't know. Did it open up more ideas? I hope so.
James / Nezeray