Speaking of categorizing errors, I categorize this as a "pre-backgame" position. White has an anchor and a half, and hitting gives her the chance of making a second anchor, so we have to assess that tradeoff.
According to the rollout, the DMP play is clear: anchor. For money, the rollout says that the extra (net) gammon wins of the double hit (or even hit and cover) outweigh the extra losses, and anchoring is a whopper.

              
 
              
 | | White is Player 2
score: 0 pip: 164 | | 1 point match | pip: 137 score: 0
Blue is Player 1 | |
| XGID=-A-aBbDBB-b-bB---bab-baA-A:0:0:1:53:0:0:0:1:10 |
| Blue to play 53 |
| 1. | Rollout1 | Bar/20 23/20 | eq: +0.131 |
| Player: Opponent: | 56.54% (G:22.24% B:0.72%) 43.46% (G:7.68% B:0.60%) | Conf.: ± 0.005 (+0.126...+0.136) - [100.0%] Duration: 19 minutes 28 seconds |
|
| 2. | Rollout1 | Bar/22* 23/18* | eq: +0.089 (-0.042) |
| Player: Opponent: | 54.46% (G:34.61% B:2.97%) 45.54% (G:9.48% B:0.86%) | Conf.: ± 0.008 (+0.082...+0.097) - [0.0%] Duration: 30 minutes 47 seconds |
|
| 3. | Rollout1 | Bar/22* 6/1 | eq: +0.050 (-0.081) |
| Player: Opponent: | 52.49% (G:35.37% B:1.96%) 47.51% (G:10.56% B:1.15%) | Conf.: ± 0.007 (+0.043...+0.057) - [0.0%] Duration: 25 minutes 37 seconds |
|
| |
1 1296 Games rolled with Variance Reduction. Dice Seed: 271828 Moves: 3-ply, cube decisions: XG Roller
|
eXtreme Gammon Version: 2.10, MET: Kazaross XG2
For money:

              
 
              
 | | White is Player 2
score: 0 pip: 164 | | Unlimited Game | pip: 137 score: 0
Blue is Player 1 | |
| XGID=-A-aBbDBB-b-bB---bab-baA-A:0:0:1:53:0:0:0:0:10 |
| Blue to play 53 |
| 1. | Rollout1 | Bar/22* 23/18* | eq: +0.401 |
| Player: Opponent: | 55.37% (G:28.62% B:0.86%) 44.63% (G:10.07% B:0.44%) | Conf.: ± 0.010 (+0.391...+0.410) - [100.0%] Duration: 1 hour 53 minutes |
|
| 2. | Rollout1 | Bar/22* 6/1 | eq: +0.340 (-0.061) |
| Player: Opponent: | 53.77% (G:30.15% B:0.65%) 46.23% (G:11.21% B:0.54%) | Conf.: ± 0.011 (+0.328...+0.351) - [0.0%] Duration: 1 hour 45 minutes |
|
| 3. | Rollout2 | Bar/20 23/20 | eq: +0.289 (-0.112) |
| Player: Opponent: | 57.09% (G:16.57% B:0.31%) 42.91% (G:8.91% B:0.38%) | Conf.: ± 0.014 (+0.275...+0.303) - [0.0%] Duration: 21 minutes 50 seconds |
|
| |
1 5184 Games rolled with Variance Reduction. Dice Seed: 271828 Moves: 3-ply, cube decisions: XG Roller
2 1296 Games rolled with Variance Reduction. Dice Seed: 271828 Moves: 3-ply, cube decisions: XG Roller
|
eXtreme Gammon Version: 2.10