Daniel nicely pointed out how superficial my initial analysis was. For the first set of variants let's remove our blot on the 1pt. Then it seems that it's all about distribution of spares.

              
 
              
 | | White is Player 2
score: 0 pip: 139 | Unlimited Game Jacoby | pip: 133 score: 0
Blue is Player 1 | | | XGID=--a-a-ECBa-BcB---bAc---bb-:0:0:1:42:0:0:1:0:10 | | Blue to play 42 | | | 1. | Rollout1 | 8/4* 6/4 | eq: +0.420 | | Player: Opponent: | 62.10% (G:21.27% B:1.48%) 37.90% (G:15.32% B:0.37%) | Conf.: ± 0.004 (+0.416...+0.423) - [100.0%] Duration: 36 minutes 03 seconds |
| | 2. | Rollout1 | 13/9* 6/4* | eq: +0.409 (-0.010) | | Player: Opponent: | 62.23% (G:17.91% B:1.13%) 37.77% (G:17.13% B:0.95%) | Conf.: ± 0.004 (+0.405...+0.414) - [0.0%] Duration: 35 minutes 17 seconds |
| | 3. | Rollout2 | 13/9* 11/9 | eq: +0.311 (-0.109) | | Player: Opponent: | 60.77% (G:12.61% B:0.75%) 39.23% (G:14.88% B:0.41%) | Conf.: ± 0.016 (+0.295...+0.327) - [0.0%] Duration: 4 minutes 07 seconds |
| | | 1 15552 Games rolled with Variance Reduction. Dice Seed: 1259354 Moves: 3-ply, cube decisions: XG Roller
2 1296 Games rolled with Variance Reduction. Dice Seed: 1259354 Moves: 3-ply, cube decisions: XG Roller
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eXtreme Gammon Version: 2.03

              
 
              
 | | White is Player 2
score: 0 pip: 139 | Unlimited Game Jacoby | pip: 135 score: 0
Blue is Player 1 | | | XGID=--a-a-DCCa-BcB---bAc---bb-:0:0:1:42:0:0:1:0:10 | | Blue to play 42 | | | 1. | Rollout1 | 8/4* 6/4 | eq: +0.799 | | Player: Opponent: | 72.37% (G:19.80% B:1.40%) 27.63% (G:7.81% B:0.15%) | Conf.: ± 0.015 (+0.783...+0.814) - [100.0%] Duration: 3 minutes 01 second |
| | 2. | Rollout1 | 13/9* 6/4* | eq: +0.460 (-0.339) | | Player: Opponent: | 63.78% (G:17.50% B:1.02%) 36.22% (G:16.60% B:0.88%) | Conf.: ± 0.013 (+0.447...+0.473) - [0.0%] Duration: 3 minutes 05 seconds |
| | 3. | Rollout1 | 13/9* 11/9 | eq: +0.397 (-0.402) | | Player: Opponent: | 62.91% (G:12.79% B:0.77%) 37.09% (G:14.16% B:0.34%) | Conf.: ± 0.015 (+0.382...+0.412) - [0.0%] Duration: 4 minutes 12 seconds |
| | 4. | Rollout1 | 11/9* 8/4* | eq: +0.378 (-0.421) | | Player: Opponent: | 61.54% (G:18.04% B:1.13%) 38.46% (G:18.02% B:0.88%) | Conf.: ± 0.013 (+0.364...+0.391) - [0.0%] Duration: 3 minutes 13 seconds |
| | | 1 1296 Games rolled with Variance Reduction. Dice Seed: 1259354 Moves: 3-ply, cube decisions: XG Roller
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eXtreme Gammon Version: 2.03

              
 
              
 | | White is Player 2
score: 0 pip: 139 | Unlimited Game Jacoby | pip: 138 score: 0
Blue is Player 1 | | | XGID=--a-a-DCBa-CcB---bAc---bb-:0:0:1:42:0:0:1:0:10 | | Blue to play 42 | | | 1. | Rollout1 | 13/9* 11/9 | eq: +0.560 | | Player: Opponent: | 66.30% (G:12.83% B:0.78%) 33.70% (G:10.96% B:0.15%) | Conf.: ± 0.015 (+0.544...+0.575) - [100.0%] Duration: 4 minutes 20 seconds |
| | 2. | Rollout1 | 18/14 11/9* | eq: +0.446 (-0.114) | | Player: Opponent: | 63.43% (G:12.28% B:0.71%) 36.57% (G:13.25% B:0.22%) | Conf.: ± 0.014 (+0.432...+0.460) - [0.0%] Duration: 4 minutes 14 seconds |
| | 3. | Rollout1 | 13/9* 6/4* | eq: +0.441 (-0.119) | | Player: Opponent: | 63.33% (G:16.96% B:1.05%) 36.67% (G:16.63% B:0.75%) | Conf.: ± 0.015 (+0.426...+0.457) - [0.0%] Duration: 3 minutes 15 seconds |
| | 4. | Rollout1 | 8/4* 6/4 | eq: +0.420 (-0.140) | | Player: Opponent: | 62.50% (G:19.30% B:1.35%) 37.50% (G:15.39% B:0.30%) | Conf.: ± 0.013 (+0.406...+0.433) - [0.0%] Duration: 3 minutes 17 seconds |
| | | 1 1296 Games rolled with Variance Reduction. Dice Seed: 1259354 Moves: 3-ply, cube decisions: XG Roller
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eXtreme Gammon Version: 2.03

              
 
              
 | | White is Player 2
score: 0 pip: 139 | Unlimited Game Jacoby | pip: 140 score: 0
Blue is Player 1 | | | XGID=--a-a-DCBa-BcC---bAc---bb-:0:0:1:42:0:0:1:0:10 | | Blue to play 42 | | | 1. | Rollout1 | 13/9* 11/9 | eq: +0.545 | | Player: Opponent: | 66.18% (G:11.70% B:0.71%) 33.82% (G:11.09% B:0.15%) | Conf.: ± 0.016 (+0.528...+0.561) - [100.0%] Duration: 4 minutes 41 seconds |
| | 2. | Rollout1 | 13/9* 6/4* | eq: +0.491 (-0.054) | | Player: Opponent: | 64.48% (G:17.41% B:1.04%) 35.52% (G:15.31% B:0.36%) | Conf.: ± 0.014 (+0.478...+0.505) - [0.0%] Duration: 3 minutes 20 seconds |
| | 3. | Rollout1 | 13/9* 9/7 | eq: +0.402 (-0.143) | | Player: Opponent: | 62.52% (G:10.99% B:0.70%) 37.48% (G:11.55% B:0.18%) | Conf.: ± 0.014 (+0.388...+0.416) - [0.0%] Duration: 5 minutes 00 second |
| | 4. | Rollout1 | 8/4* 6/4 | eq: +0.398 (-0.147) | | Player: Opponent: | 61.77% (G:18.48% B:1.11%) 38.23% (G:15.81% B:0.32%) | Conf.: ± 0.013 (+0.385...+0.411) - [0.0%] Duration: 3 minutes 25 seconds |
| | | 1 1296 Games rolled with Variance Reduction. Dice Seed: 1259354 Moves: 3-ply, cube decisions: XG Roller
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eXtreme Gammon Version: 2.03