Therein lies the problem. Bets really require a set of undeniable parameters to get a payoff. Regardless, I'll say this if you are in agreement, if he never gets behind the wheel of an F1 car and starts a race then I'll buy you a case of beer(not Blatz, Genesse, Schlitz or some other nasty frat party brand, but not some small micro brew either) and you can buy me the equivilant in premium gas so I can take a little drive. As he is relatively young, what do you think 4 years or so for one of us to make the claim of victory. As you are also a grey beard I'm sure neither of us will remember the bet in 4 years or for that matter 3 days. On his ability to win, let's first get him behind a wheel and on the grid. Then we can set the wager on him on a podium .
I'm old enough to know and understand Rossi's achievements in Grand Prix motorcycle racing. And I'm old enough to appreciate what Rossi means to the Italians!
Your conditions are reasonable, but F1 isn't: Just look at who is rumored to be hired as "driver" by USF1. If you bring money (your own or sponsors'), you get a seat these days. Superlicense will come as an afterthought courtesy of the FIA. Rossi has certainly charisma, fans and sponsorships and with one second off the pace he is not without some talent. Enough to grant him a license at least. So could I imagine him in a F1? Absolutely. Would he win anything (under normal conditions)? No way. So I'll have to skip your bet for him making it into F1. But if he does, I'll be the first in line to bet against him achieving anything in it. Given that Ferrari put even a total looser like BADoer into a Ferrari at a GP this season, it is not unthinkable they would be willing to put Rossi into a car. 3rd Ferrari at Monza anybody? Quite possible. And Bernie would love it as his ticket sales would go throw the roof.
I think Rossi could significantly improve his times in an F1 effort, given time. He has unbelievable instincts and understanding of dynamics, and he is not a dead fish like half the current F1 pool. And he would probably like to eclipse John Surtees record with a F1 WDC. Don't sell the man short. Everyone that has got burned.
Eddie Undera-Cheever would actually have some F1 experience. No: http://joesaward.wordpress.com/2009/11/20/jose-maria-lopez-and-usf1/ Compared to this guy, Rossi looks like a good pick.
Wasn't Winsor one of the bunch of folks who spoke about bringing up new young talent. Goes back to F1 being about bucks and not much else. Regardless, I will be happy to part with my dollars in Canada if they gey it resolved.