Why is my play 22/21 22/20 4/3 so wrong here compared to the other plays? Is it really that less flexible than the other options (makes me have bad 3's coming up). What am I missing about this position?

Thanks

Ahead in the race with four men back is awkward. Because of this, perhaps the top priority strategically is to get the furthest back men moving. Toward this end, I am inclined to want men on 21 and 22, so I can play both 6 and 5 from the back. So I will try 22/21 6/4 6/5.

Of course I am no pro, and won't be surprised if this totally flops on analysis.

Putting a checker out of play with 4/3 is called killing the checker. This is almost always bad. Black might close his board if white is unlucky, otherwise white is very likely to leave a blot after being in the game again, and in this case with white's board the more men back the better. Black hopes to move up to his outerboard gradually.Though being 19 points ahead in the race it costs him only 0.04 compared to saving his checker by playing 22/21 6/4 6/5. And 22/20 22/21 4/3 costs .27? Spreading over 3 back points gives more flexibility than spreading over 2 points, the farther behind the checker the better (referring to 22 point), and a possible bearing off disadvantage with an empty four point. But that at hindsight. I would have slotted the 6 point.

The only thing bad about your play is that there is a better play.

Try 22/21 6/4 6/5. Now you have all 6s, 5s, 4s, 3s, and 2s to escape back checkers, and because you cleared from the back, your board doesn't have a gap in it. It's a better play on both sides of the board.