I once thought this was a good idea as well, but what DED said in post 6 is very real, as are the number of fakes floating around out there.
The only way I would ever do one of these is if I knew and had dealt with all the participants, and they'd all been sourcing their own purchases, and had boxcodes to provide (again, like what DED mentioned).
Passes are intended to be fun however, an u may very well have a list of participants here willing to proceed knowing all that. I'm sure cigars new to each could still be tried...and likely fakes wouldn't even find their way into the boxpass.... Ya just never know.
I passed on this simply due to time, and life getting in the way. And if I want smokes anymore these days, I'll just buy em. But, I'm trying my best to just smoke what I already have. So far, so good.
Good luck with the pass though, and I do hope it works out. I'll certainly follow the thread should that happen.