No. It's not worth $1000, in my opinion.
I've gone to about 20 GenCons though, so I suppose I should clarify.
This year, my hotel is going to run me over $700. I am bringing my two sons, at least one of their friends, and probably at least one other friend. They'll be staying in my room. One of my sons is 12, he's not paying anything, obviously. My friend will chip in some cash. My 17-year-old and his same-aged friends, will be chipping in a little.
We buy food from the local grocery and take it with us in a cooler. I know that not everyone can drive to GenCon. Some years, I've bought food at an Indianapolis grocery and taken it to the hotel. There are ways around the high food costs.
I play in a few games--they're not that expensive. I buy a set or three of dice (they are a little pricey, but it's my annual indulgence). I don't tend to buy books or anything like that because I'd prefer to by them at my local game store and keep those guys in business.
Overall, it costs me around $1,000. But, this is for at least four people, not for just me. If it cost me $4,000 to take 4 people; I wouldn't go.
Dave