I would be interested but have a number of questions:
1 - how many people would we need to make this happen?
2 - Who determines seating? I know that most of the FTers on this board would not be happy with middle coach seats in a 744/742 (including myself).
3 - who determines who gets biz class seating? Less important for short hops, but much more if flight is over say 1 hour.
In response to your questions:
1 - the price I'd be willing to pay would be based on distance. It's a very difficult question to answer. Let's assume we get 400 people to buy into this. If eveyone paid $300 for it, we're only dealing with $120k...I seriously doubt that would be enough for a charter. Would most likely be double or triple that which would make it unaffordable for most of us.
2 - Yes, but things would have to be spelled out pretty specifically in a contract of sorts.
3 - I like the idea of a lakeside cookout somewhere (provided there was a vegetarian option). If it's wintertime, how about a hop to somewhere sunny (FL?) for an oceanside cookout??
Without knowing how much it would cost to charter a 744/742, it's going to be very difficult to put numbers together. If it's within reason, definitely count me in!