Palaner asked: Are four days of pure, unadulterated gaming worth $1000+ dollars to come down, find a hotel, find food, pay to get in, pay for certain events, pay for some merchandise, etc.?
Is Gen Con even accessible to people who don't exactly have money to burn?
I've only been to GenCon once, 2002, the last year in Milwaukee.
To answer your first question, is it worth $1000, I would have to say yes. I went with two friends, and we had a great time. Went to the Safe House a couple of times, went to a nice brew pub, and visited a dingy bar with cheap beer and loud music. We also played some games we have never seen before, I got to attend a few fantastic seminars by Monte Cook, and I bought a bunch of stuff in the dealer's room.
Your second question is difficult to answer. As a lot of people have noted, once you have paid your admission, you can see a LOT without paying more. I didn't play in any pick-up games, but there were people playing all over the place, for free. As well, you don't have to buy any swag or play in any pay games.
My advice is to attend if you can afford what you want to do there. I would never go into debt for GenCon, but the only debts I ever carry over time are car loans and mortgages, so I am fairly conservative when it comes to money (comes with age!), YMMV.
I plan on attending GenCon again, perhaps in 2007, but I will stay in a nice hotel close to the event, eat and drink as desired, and perhaps this time I will buy the Parkinson print that I had my eye on last time!!