My issue with this is that you need to spend so much time after the round correcting the data. For instance, you need to remember the times you used your putter but weren't on the green, the bunker shots, penalties, etc. The concept sounds great, and if they figured out a way to limit the post-round data correction I'd be in.
You have to play him, don't you? And there should money on it. If he really thinks he's as good as he has advertised that he is, he has to take the bet. And at an 11 handicap, you'll probably take him apart out there.
I enjoy golf for what it is. I always say that it's the hardest thing I do voluntarily. Good scores are great, and I tend not to get too frustrated on the course. I just thoroughly enjoy being out there playing.
Going from a 2 handicap to shanks for a year, would be rough, though.