At the Viking Classic this year, Ray gave a talk on taking the cube in general and, as a teaser the day before, came by my board between matches and showed me this one from a money game he had earlier in the day.
(He said he would sign up and post it himself... but it seems that has yet to happen . So I'll just post it for him )
Looks like white has an easy redouble to 32. Having 12 checkers off makes me feel like this should be a drop. If black takes with the 21 they're gonna have to rip checkers pretty aggressively to catch up. Black would probably welcome being hit to try and get another checker back. Fun position! Pretty rare to see a double from the bar closed out.
It's more common to be doubling this situation from Black's perspective, so I start with references for that. Each checker on the bar counterbalances 5 checkers they have off: with 1 checker on the bar, if they have 5 off it's a double, or if 2 on the bar, 10 off is a double. (It also depends on spare distribution, and the second checker on the bar is stronger for Black, but that gets us in the ballpark.)
So for Black to double in this position, he'd need 7 checkers off. But, White's on roll, which is harder to figure out. If Black's board opens soon and you enter, the market is lost. 65 or big doubles - enter... but then you also have to get missed. So I don't know, but I double and let them figure it out. For Black, I imagine how often I get to that 7 checkers off position that'll allow me to redouble. Seems often enough to take, but that's really just intuition. It'll require them to dance a couple times, which does happen. And if they just dance once, it'll be a close game, so I take.