I rolled these out before posting the problem, so some candidates that were mentioned in the responses don't appear here; sorry about that. Maybe someone else who is gung-ho can post a supplementary rollout of the missing candidates.
What I found interesting was that the strategy of "just making the 5pt" does tolerably well here, despite the double shots.
In the second position I didn't even consider the double hit because it looked so strange to me, and I played 23/18 6/4* instead.

              
 
              
 | | White is Player 2
score: 0 pip: 144 | Money session Jacoby | pip: 144 score: 0
Blue is Player 1 | |
| XGID=--aaB-CBC-A-cB---d-d--Bb--:1:-1:1:52:0:0:1:0:10 |
| Blue to play 52 |
| 1. | Rollout1 | 10/5 7/5 | eq: +0.279 |
| Player: Opponent: | 63.62% (G:22.88% B:0.73%) 36.38% (G:8.12% B:0.32%) | Conf: ± 0.010 (+0.269...+0.289) Duration: 3 hours 25 minutes |
|
| 2. | Rollout1 | 10/3* | eq: +0.264 (-0.015) |
| Player: Opponent: | 63.25% (G:22.53% B:0.80%) 36.75% (G:8.80% B:0.34%) | Conf: ± 0.010 (+0.254...+0.274) Duration: 3 hours 29 minutes |
|
| 3. | Rollout1 | 13/11 8/3* | eq: +0.225 (-0.054) |
| Player: Opponent: | 62.81% (G:22.16% B:0.92%) 37.18% (G:11.39% B:0.64%) | Conf: ± 0.013 (+0.212...+0.238) Duration: 3 hours 40 minutes |
|
| 4. | Rollout1 | 13/11 13/8 | eq: +0.170 (-0.108) |
| Player: Opponent: | 61.28% (G:18.32% B:0.64%) 38.72% (G:8.30% B:0.34%) | Conf: ± 0.010 (+0.160...+0.180) Duration: 3 hours 09 minutes |
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| |
1 2162 Games rolled with Variance Reduction. Dice Seed: 2 Moves and cube decisions: 3 ply
|
eXtreme Gammon Version: 1.21
This one was rolled out with XG2.

              
 
              
 | | White is Player 2
score: 0 pip: 156 | Money session Jacoby | pip: 151 score: 0
Blue is Player 1 | |
| XGID=-a--a-EBC-A-cB--bc-e---AA-:0:0:1:52:0:0:1:0:10 |
| Blue to play 52 |
| 1. | Rollout1 | 6/4* 6/1* | eq: -0.030 |
| Player: Opponent: | 48.96% (G:17.29% B:0.53%) 51.04% (G:15.59% B:1.12%) | Conf: ± 0.008 (-0.038...-0.022) Duration: 1 hour 17 minutes |
|
| 2. | Rollout1 | 10/5 7/5 | eq: -0.055 (-0.025) |
| Player: Opponent: | 47.91% (G:15.96% B:0.61%) 52.09% (G:13.92% B:0.78%) | Conf: ± 0.009 (-0.064...-0.046) Duration: 1 hour 06 minutes |
|
| 3. | Rollout1 | 23/18 10/8 | eq: -0.063 (-0.034) |
| Player: Opponent: | 48.94% (G:11.96% B:0.56%) 51.06% (G:14.40% B:0.55%) | Conf: ± 0.008 (-0.071...-0.055) Duration: 1 hour 10 minutes |
|
| 4. | Rollout1 | 23/18 6/4* | eq: -0.081 (-0.051) |
| Player: Opponent: | 48.69% (G:14.26% B:0.77%) 51.31% (G:17.62% B:1.21%) | Conf: ± 0.009 (-0.090...-0.072) Duration: 1 hour 15 minutes |
|
| 5. | Rollout1 | 10/5 6/4* | eq: -0.082 (-0.052) |
| Player: Opponent: | 48.57% (G:14.19% B:0.71%) 51.43% (G:16.73% B:1.16%) | Conf: ± 0.009 (-0.091...-0.073) Duration: 1 hour 17 minutes |
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| |
1 5184 Games rolled with Variance Reduction. Moves: 3 ply, cube decisions: XG Roller
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