Now, back up a little. How many of you, who have replied, have actually done it? Didn't think so.....
The simple fact that is so far from being cost effective, that it would never be done...
Formation flying. You'll have to teach everyone who might participate how to do it. Have a think about it. How do you handle a rejoin...at night....or in cloud ('cos the weather will never conveniently move so that you can tank). The aviation world spends its time keeping aircraft apart, and here you want two within about 30 feet of each other. You'll note that all of the aircraft involved belong to air forces...in particular, one air force.
Insurance. Ha.
The turbulence from the lead aircraft is a huge issue.
Yes, it can be done by big aircraft. But, it's actually done by a very small group of people, who basically do it every working day. And even then they come together every now and then. A much more cost effective, and way safer, solution is to simply charge more, and carry less people.