1) Making the 5pt looked clear after some shorter early analysis and it also rolled out right with stronger settings. However another play being so close to best was not quite what I intended when I posed the problem. Surprising to me was how strong slotting the 5pt with 13/11 actually was and how bad splitting was with 24/23 13/11.
  White is Player 2
score: 6 pip: 154  9 point match  pip: 160 score: 5
Blue is Player 1  
XGID=bEBBcDacdbB:0:0:1:21:5:6:0:9:10 
Blue to play 21 
1.  Rollout^{1}  7/5 6/5  eq: +0.030 
 Player: Opponent:  47.29% (G:14.56% B:1.19%) 52.71% (G:19.09% B:2.64%)  Conf.: ± 0.011 (+0.020...+0.041)  [91.2%] Duration: 3 hours 26 minutes 

2.  Rollout^{1}  13/11 6/5  eq: +0.020 (0.010) 
 Player: Opponent:  47.73% (G:13.65% B:1.20%) 52.27% (G:20.29% B:3.16%)  Conf.: ± 0.011 (+0.009...+0.031)  [8.8%] Duration: 3 hours 40 minutes 

3.  Rollout^{2}  24/23 13/11  eq: 0.146 (0.176) 
 Player: Opponent:  44.99% (G:12.72% B:1.26%) 55.01% (G:21.32% B:1.73%)  Conf.: ± 0.025 (0.171...0.120)  [0.0%] Duration: 33 minutes 30 seconds 

4.  4ply  13/10  eq: 0.156 (0.186) 
 Player: Opponent:  44.36% (G:12.28% B:0.61%) 55.64% (G:18.24% B:1.13%)  


^{1} 5184 Games rolled with Variance Reduction. Dice Seed: 11290312 Moves: 3ply, cube decisions: XG Roller Search interval: Huge
^{2} 775 Games rolled with Variance Reduction. Dice Seed: 11290312 Moves: 3ply, cube decisions: XG Roller Search interval: Huge

eXtreme Gammon Version: 2.10, MET: Kazaross XG2
2) A solid Double and a solid Take. I was actually White in the diagram and passed the the cube from my opponent. Not doubling this position turns out to be as big a mistake as passing it.
  White is Player 2
score: 0 pip: 98  Unlimited Game  pip: 116 score: 0
Blue is Player 1  
XGID=aBBCBaBAAaabbbcbB:0:0:1:D:0:0:0:0:10 
Blue on roll, cube action? 
Analyzed in Rollout  No double  Double/Take 
Player Winning Chances:  71.80% (G:18.00% B:0.91%)  72.31% (G:18.31% B:0.96%) 
Opponent Winning Chances:  28.20% (G:13.45% B:0.59%)  27.69% (G:13.61% B:0.61%) 
Cubeless Equities  +0.485  +0.993 
Cubeful Equities 
No double:  +0.652 (0.176)  ±0.009 (+0.644..+0.661) 
Double/Take:  +0.828  ±0.012 (+0.816..+0.841) 
Double/Pass:  +1.000 (+0.172) 

Best Cube action: Double / Take 
Rollout details 
1980 Games rolled with Variance Reduction. Dice Seed: 11290312 Moves: 3ply, cube decisions: XG Roller Search interval: Huge


Double Decision confidence:  100.0% 
Take Decision confidence:  100.0% 
Duration: 42 minutes 15 seconds 
eXtreme Gammon Version: 2.10
3) Once you decide 15/6 is much weaker than 21/15 then the 3 plays itself.
  White is Player 2
score: 0 pip: 153  Unlimited Game  pip: 130 score: 0
Blue is Player 1  
XGID=BCaCbcEAcdbA:0:0:1:63:0:0:0:0:10 
Blue to play 63 
1.  Rollout^{1}  21/15 13/10  eq: 0.185 
 Player: Opponent:  45.73% (G:13.31% B:0.29%) 54.27% (G:17.42% B:0.67%)  Conf.: ± 0.022 (0.207...0.163)  [100.0%] Duration: 17 minutes 21 seconds 

2.  Rollout^{2}  15/6  eq: 0.254 (0.069) 
 Player: Opponent:  43.70% (G:15.67% B:0.39%) 56.30% (G:17.69% B:0.57%)  Conf.: ± 0.022 (0.276...0.231)  [0.0%] Duration: 16 minutes 47 seconds 

3.  Rollout^{2}  21/15 6/3  eq: 0.257 (0.072) 
 Player: Opponent:  44.43% (G:12.60% B:0.31%) 55.57% (G:19.40% B:0.68%)  Conf.: ± 0.022 (0.279...0.235)  [0.0%] Duration: 16 minutes 53 seconds 


^{1} 537 Games rolled with Variance Reduction. Dice Seed: 11290312 Moves: 3ply, cube decisions: XG Roller Search interval: Huge
^{2} 536 Games rolled with Variance Reduction. Dice Seed: 11290312 Moves: 3ply, cube decisions: XG Roller Search interval: Huge

eXtreme Gammon Version: 2.10
4) Preclearing the bar was easy for most. OtB I talked myself into clearing the back point. I need more work on bearins it seems.
  White is Player 2
score: 4 pip: 117  5 point match Crawford  pip: 82 score: 0
Blue is Player 1  
XGID=bCBCCBBabcbbba:0:0:1:31:0:4:1:5:10 
Blue to play 31 
1.  Rollout^{1}  7/6 7/4  eq: +0.808 
 Player: Opponent:  89.84% (G:11.70% B:0.12%) 10.16% (G:0.32% B:0.02%)  Conf.: ± 0.003 (+0.804...+0.811)  [100.0%] Duration: 5 minutes 46 seconds 

2.  Rollout^{1}  9/5  eq: +0.731 (0.076) 
 Player: Opponent:  86.14% (G:8.09% B:0.18%) 13.86% (G:0.61% B:0.07%)  Conf.: ± 0.003 (+0.728...+0.735)  [0.0%] Duration: 4 minutes 56 seconds 


^{1} 648 Games rolled with Variance Reduction. Dice Seed: 11290312 Moves: 3ply, cube decisions: XG Roller Search interval: Huge

eXtreme Gammon Version: 2.10, MET: Kazaross XG2
5) Bringing more material close and minimising the damage from a 4, particularly 44, appears to be the key to this problem. Initial analysis had 13/8 4/3 as a firm favourite by a larger margin, a longer and stronger rollout makes other plays close.
  White is Player 2
score: 4 pip: 145  5 point match  pip: 110 score: 1
Blue is Player 1  
XGID=cBBABBAACcbeAb:1:1:1:51:1:4:0:5:10 
Blue to play 51 
1.  Rollout^{1}  13/8 4/3  eq: +2.144 
 Player: Opponent:  90.66% (G:63.45% B:5.76%) 9.34% (G:1.29% B:0.06%)  Conf.: ± 0.004 (+2.140...+2.149)  [100.0%] Duration: 16 minutes 49 seconds 

2.  Rollout^{1}  13/8 7/6  eq: +2.128 (0.016) 
 Player: Opponent:  90.11% (G:63.21% B:5.96%) 9.89% (G:1.59% B:0.10%)  Conf.: ± 0.005 (+2.124...+2.133)  [0.0%] Duration: 16 minutes 23 seconds 

3.  Rollout^{1}  13/12 13/8  eq: +2.122 (0.023) 
 Player: Opponent:  89.80% (G:63.17% B:5.55%) 10.20% (G:2.17% B:0.14%)  Conf.: ± 0.004 (+2.117...+2.126)  [0.0%] Duration: 15 minutes 17 seconds 

4.  Rollout^{1}  20/15 4/3  eq: +2.118 (0.026) 
 Player: Opponent:  89.93% (G:62.90% B:5.49%) 10.07% (G:1.58% B:0.10%)  Conf.: ± 0.004 (+2.114...+2.123)  [0.0%] Duration: 16 minutes 45 seconds 

5.  Rollout^{2}  20/15 13/12  eq: +2.106 (0.039) 
 Player: Opponent:  89.02% (G:63.17% B:3.87%) 10.98% (G:2.69% B:0.22%)  Conf.: ± 0.006 (+2.100...+2.112)  [0.0%] Duration: 27.5 seconds 

6.  Rollout^{3}  20/15 5/4  eq: +2.083 (0.062) 
 Player: Opponent:  88.95% (G:62.13% B:3.76%) 11.05% (G:2.09% B:0.15%)  Conf.: ± 0.007 (+2.076...+2.089)  [0.0%] Duration: 23.8 seconds 


^{1} 2592 Games rolled with Variance Reduction. Dice Seed: 11290312 Moves: 3ply, cube decisions: XG Roller Search interval: Huge
^{2} Truncated at 11 moves using 4ply. 216 Games rolled with Variance Reduction. Dice Seed: 44171799 Moves and cube decisions: 3ply Red
^{3} Truncated at 11 moves using XG Roller. 216 Games rolled with Variance Reduction. Dice Seed: 1150556 Moves and cube decisions: 3ply Red

eXtreme Gammon Version: 2.10, MET: Kazaross XG2