The bot says to hit twice. I'm not sure how to generalize here, but certainly hitting twice gives White no choice about how to play most of her rolls, whereas hitting once will often give White some flexibility in choosing how to set up a good defensive position.
Rollout courtesy of a friend of mine with XG2, since I didn't trust XG1 as much with a proto-backgame like this one (not to mention that it would take forever on my slow computer).

              
 
              
 | | White is Player 1
score: 0 pip: 197 | | Money session | pip: 164 score: 0
Blue is Player 2 | |
| XGID=-baa--E-C--AdDa--c-ba-A--A:0:0:1:44:0:0:0:0:10 |
| Blue to play 44 |
| 1. | Rollout1 | Bar/21 22/14* 6/2* | eq: +0.415 |
| Player: Opponent: | 55.93% (G:25.30% B:3.12%) 44.07% (G:9.04% B:0.41%) | Conf: ± 0.008 (+0.407...+0.423) Duration: 5 hours 28 minutes |
|
| 2. | Rollout1 | Bar/21 13/9 6/2*(2) | eq: +0.375 (-0.040) |
| Player: Opponent: | 54.41% (G:26.92% B:3.61%) 45.59% (G:9.53% B:0.46%) | Conf: ± 0.007 (+0.368...+0.382) Duration: 3 hours 24 minutes |
|
| 3. | Rollout1 | Bar/21 22/14* 14/10 | eq: +0.364 (-0.051) |
| Player: Opponent: | 55.48% (G:23.53% B:1.99%) 44.52% (G:9.13% B:0.39%) | Conf: ± 0.007 (+0.357...+0.371) Duration: 4 hours 30 minutes |
|
| 4. | Rollout1 | Bar/21 22/14* 13/9 | eq: +0.340 (-0.075) |
| Player: Opponent: | 54.73% (G:23.76% B:2.15%) 45.27% (G:9.63% B:0.45%) | Conf: ± 0.008 (+0.332...+0.348) Duration: 5 hours 39 minutes |
|
| 5. | Rollout1 | Bar/21 11/7 6/2*(2) | eq: +0.335 (-0.080) |
| Player: Opponent: | 53.72% (G:25.26% B:3.17%) 46.28% (G:10.18% B:0.46%) | Conf: ± 0.007 (+0.328...+0.342) Duration: 4 hours 10 minutes |
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| |
1 10368 Games rolled with Variance Reduction. Moves: 3 ply, cube decisions: XG Roller
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eXtreme Gammon