The problem is is that a 12 handicap isnt going to play bogey golf in this format. If OP was like a 3 handicap, I think this is the easiest bet in the world

But arent you assuming he is going to hit a good and bad shot often and not two good shots most of the time?
I am a 13, and my first reaction was this was an easy bet. I am now thinking 100 is a good number. But I am not convinced Bo isnt right and its a no-win.
I am a 13 because I make mistakes. But a majority of the time I dont make mistakes. And having to hit two balls off the tee isnt going to really change my score. But I see where basically two putting everything is bad.

If that hole was representative of my worst set of shots on a hole I wouldn't be a 15. That hole I laid out would be pretty much a good result. At least a couple times it would go a little like this:

pump drive oob. hit one of two drives in the rough. hit fourth shot into bunker. hit both out but leave fifth shot 45 feet away. three putt. boom, 8.

I'm definitely propping my friend to do this vs me in a 9 hole match. We are both around 0-1.

I'll include a TR once we get it organized.

more like this, no?

Yea, this just reminded me of something. I used to play with a group of guys where we allowed everyone to have one "re-do" each round. That is, you could have another player re-take a shot at any point. It so mentally destroyed someone when they stuck it close, had to re-hit and put it in the bunker. This is like being made to re-do every shot!

It's even worse than that. You're made to re-do every shot, then have to choose the worse one. (Sometimes your re-do is better than your first)

so you have to hole out twice to chalk up a score right?

If Fred Funk had to hit two balls off each tee, and choose the worst one, it would really change his score.

I think the typical golfer doesn't realize how "lucky" their good shots are. I am around an 8 and when I hit a green from lets say 180+ yards I usually think "nice, I'm getting good", I rarely think "wow that was lucky", if I had to hit it again and take the worst one reality would set in pretty quick as to my probability of hitting some of those shots

I'm a 13,4 and I think that's doable

that shows how little I know about this game.
Going to try this next time I'm on a course

If the course has little trouble, you are a good lag putter, and are money from 6-10 ft, no problem. Then again, you would probably not be a 12. You would also most certainly want to play more conservatively than normal. Tbh, I'm a 7, tend to bunt it around in pay, and I don't think id take the bet to break 95...

Sure, but I am a former golf pro, and do understand golf course management. I have a good grasp of the course and I know where to miss. You won't see me shortsided with a very difficult up and down unless I get unlucky.

I thought after a two year hiatus my shortgame was going to be shaky. In fact I'm surprised because I feel like I'm better around the greens and can't control my tee shots anymore. My ball striking with irons seems good still, but I'm not able to control my ball flights like I used to.

I think my strategy will be to play safe bogey golf, and with the occasional par and double I don't see why this won't be doable. My practice round will be Sunday, so I'll update for all those who are curious.

Great point about being repeatedly discouraged. The tilt factor is huge here. You would never get comfortable in the round and for must that would be a killer

I'm in the no chance bucket.

I would expect a 13 to hit about 2 fairways in this format, probably about the same number of greens.

Assuming that you can get it within 40 yards of the hole in regulation (which won't happen at least a few times during the round), I would think a 13 would get the pitch shot inside 30 feet less than 2 out of 10 times.

And from 30+ feet I expect 3 putts to outnumber 2 putts.

All that adds up to averaging a double on each hole.

So even on a golf course with no OB or water hazards I think there is basically zero chance. If the course is at all difficult the score will be 115+ no problem.