I'm impressed that Joe Russell finds it obvious that clearing wins more often. Ripping leaves only 4 immediate blotting rolls instead of 12 and also takes off two checkers, which helps if we are hit. It might win marginally more games if White's forward position were perfect (see variant below). Of course, ripping also leaves us with more long-term danger since several rolls that don't blot immediately leave us with an awkward distribution that could blot later. I think that part of the story is that if we're going to leave shots then we want to do it now rather than later, when White's board will probably be stronger.
For money, backgammons matter, and the rollout below suggests that ripping comes out ahead, though not by a large margin.

              
 
              
 | | White is Player 2
score: 5 pip: 163 | 7 point match | pip: 39 score: 4
Blue is Player 1 | |
XGID=-BeCCBA----------aacb-a-b-:1:-1:1:33:4:5:0:7:10 |
Blue to play 33 |
1. | Rollout1 | 6/3 4/1(3) | eq: +1.497 |
| Player: Opponent: | 87.48% (G:78.44% B:64.33%) 12.52% (G:0.00% B:0.00%) | Conf.: ± 0.005 (+1.492...+1.501) - [100.0%] Duration: 3 minutes 26 seconds |
|
2. | Rollout1 | 6/Off 4/1 3/Off | eq: +1.445 (-0.051) |
| Player: Opponent: | 86.16% (G:75.81% B:64.31%) 13.84% (G:0.00% B:0.00%) | Conf.: ± 0.005 (+1.441...+1.450) - [0.0%] Duration: 3 minutes 29 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
Variant:

              
 
              
 | | White is Player 2
score: 5 pip: 165 | 7 point match | pip: 39 score: 4
Blue is Player 1 | |
XGID=-BeCCBA-----------bbbbb---:1:-1:1:33:4:5:0:7:10 |
Blue to play 33 |
1. | Rollout1 | 6/3 4/1(3) | eq: +1.363 |
| Player: Opponent: | 83.20% (G:73.35% B:59.56%) 16.80% (G:0.00% B:0.00%) | Conf.: ± 0.005 (+1.358...+1.368) - [86.7%] Duration: 3 minutes 26 seconds |
|
2. | Rollout1 | 6/Off 4/1 3/Off | eq: +1.359 (-0.003) |
| Player: Opponent: | 83.82% (G:71.71% B:60.53%) 16.18% (G:0.00% B:0.00%) | Conf.: ± 0.003 (+1.356...+1.363) - [13.3%] Duration: 3 minutes 24 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: 163 | Unlimited Game | pip: 39 score: 0
Blue is Player 1 | |
XGID=-BeCCBA----------aacb-a-b-:1:-1:1:33:0:0:0:0:10 |
Blue to play 33 |
1. | Rollout1 | 6/Off 4/1 3/Off | eq: +1.569 |
| Player: Opponent: | 86.73% (G:76.60% B:12.92%) 13.27% (G:0.00% B:0.00%) | Conf.: ± 0.007 (+1.562...+1.576) - [100.0%] Duration: 5 minutes 26 seconds |
|
2. | Rollout1 | 6/3 4/1(3) | eq: +1.551 (-0.018) |
| Player: Opponent: | 87.80% (G:79.05% B:5.57%) 12.20% (G:0.00% B:0.00%) | Conf.: ± 0.005 (+1.546...+1.556) - [0.0%] Duration: 4 minutes 29 seconds |
|
|
1 1296 Games rolled with Variance Reduction. Dice Seed: 271828 Moves: 3-ply, cube decisions: XG Roller
|
eXtreme Gammon Version: 2.10