This came up in our local club tourney on Saturday. I was trailing 60 Crawford, a DMPlike score. OTB, I chose clearing the 8 and that is the DMP play. 16/5 is slightly better for money even though that play is supposed to get you doubled (vs. no double after pay later), wins less often, and loses nearly as many net gammons. Two main reasons why paying now is correct (IMO): 1)Many or most players will make the small mistake of not doubling as Black after 16/5 while virtually no one doubles after clearing the 8. 2)Your position is quite a bit better after an average + sequence than if you pay later and have a good sequence. After PN and a good sequence, your position is good enough for an initial double and TCTC for a redouble. After PL and a good sequence, you don't even have an initial double. Rollouts below.
First the 65 play for money:
1.  Rollout^{1}  16/5  eq: 0.305 
 Player: Opponent:  41.15% (G:3.62% B:0.07%) 58.85% (G:14.24% B:0.56%)  Conf.: ± 0.009 (0.313...0.296)  [100.0%] Duration: 12 minutes 58 seconds 

2.  Rollout^{1}  8/3 8/2  eq: 0.327 (0.022) 
 Player: Opponent:  43.28% (G:4.11% B:0.06%) 56.72% (G:16.16% B:0.55%)  Conf.: ± 0.009 (0.336...0.318)  [0.0%] Duration: 16 minutes 46 seconds 


^{1} 2592 Games rolled with Variance Reduction. Moves: 3ply, cube decisions: XG Roller

eXtreme Gammon Version: 2.00
After 16/5, Black has a small double:
Analyzed in Rollout  No double  Double/Take 
Player Winning Chances:  58.05% (G:12.10% B:0.39%)  58.64% (G:14.04% B:0.50%) 
Opponent Winning Chances:  41.95% (G:3.40% B:0.07%)  41.36% (G:3.72% B:0.07%) 
Cubeless Equities  +0.251  +0.561 
Cubeful Equities 
No double:  +0.247 (0.038)  ±0.008 (+0.239..+0.254) 
Double/Take:  +0.285  ±0.014 (+0.271..+0.299) 
Double/Pass:  +1.000 (+0.715) 

Best Cube action: Double / Take 
Rollout details 
1296 Games rolled with Variance Reduction. Moves: 3ply, cube decisions: XG Roller


Double Decision confidence:  100.0% 
Take Decision confidence:  100.0% 
Duration: 12 minutes 45 seconds 
eXtreme Gammon Version: 2.00
After 8/2 8/3 Black isn't close to a double:
Analyzed in Rollout  No double  Double/Take 
Player Winning Chances:  56.85% (G:16.07% B:0.52%)  57.02% (G:16.25% B:0.55%) 
Opponent Winning Chances:  43.15% (G:4.17% B:0.07%)  42.98% (G:4.11% B:0.07%) 
Cubeless Equities  +0.260  +0.533 
Cubeful Equities 
No double:  +0.330  ±0.012 (+0.318..+0.342) 
Double/Take:  +0.229 (0.101)  ±0.013 (+0.215..+0.242) 
Double/Pass:  +1.000 (+0.670) 

Best Cube action: No double / Take 
Percentage of wrong pass needed to make the double decision right: 11.6% 
Rollout details 
1296 Games rolled with Variance Reduction. Moves: 3ply, cube decisions: XG Roller


Double Decision confidence:  100.0% 
Take Decision confidence:  100.0% 
Duration: 11 minutes 26 seconds 
eXtreme Gammon Version: 2.00
If you play 16/5, it goes D/T, Black misses, and you bring the straggler around to the 8. Black then plays some average number leaving a position something like this. It's then TCTC between R/NR.
Analyzed in Rollout  No redouble  Redouble/Take 
Player Winning Chances:  67.09% (G:0.97% B:0.00%)  67.39% (G:0.86% B:0.00%) 
Opponent Winning Chances:  32.91% (G:2.59% B:0.07%)  32.61% (G:2.68% B:0.08%) 
Cubeless Equities  +0.325  +0.657 
Cubeful Equities 
No redouble:  +0.535  ±0.005 (+0.530..+0.539) 
Redouble/Take:  +0.531 (0.004)  ±0.009 (+0.522..+0.540) 
Redouble/Pass:  +1.000 (+0.465) 

Best Cube action: No redouble / Take 
Percentage of wrong pass needed to make the double decision right: 0.8% 
Rollout details 
1296 Games rolled with Variance Reduction. Moves: 3ply, cube decisions: XG Roller


Double Decision confidence:  75.1% 
Take Decision confidence:  100.0% 
Duration: 9 minutes 06 seconds 
eXtreme Gammon Version: 2.00
If Black had not doubled after your 16/5 play and you had the same good sequence, you could then offer an initial double:
Analyzed in Rollout  No double  Double/Take 
Player Winning Chances:  67.09% (G:0.95% B:0.02%)  67.39% (G:0.86% B:0.00%) 
Opponent Winning Chances:  32.91% (G:2.40% B:0.07%)  32.61% (G:2.68% B:0.08%) 
Cubeless Equities  +0.327  +0.658 
Cubeful Equities 
No double:  +0.500 (0.031)  ±0.006 (+0.494..+0.505) 
Double/Take:  +0.531  ±0.009 (+0.522..+0.540) 
Double/Pass:  +1.000 (+0.469) 

Best Cube action: Double / Take 
Rollout details 
1296 Games rolled with Variance Reduction. Moves: 3ply, cube decisions: XG Roller


Double Decision confidence:  100.0% 
Take Decision confidence:  100.0% 
Duration: 11 minutes 43 seconds 
eXtreme Gammon Version: 2.00
If you paid later with 8/2 8/3, Black rolled average, you rolled a pretty good 63 (16/10 16/13), Black missed, you would not have an initial double:
Analyzed in Rollout  No double  Double/Take 
Player Winning Chances:  64.54% (G:0.90% B:0.01%)  64.83% (G:0.72% B:0.01%) 
Opponent Winning Chances:  35.46% (G:2.47% B:0.07%)  35.17% (G:2.48% B:0.08%) 
Cubeless Equities  +0.274  +0.556 
Cubeful Equities 
No double:  +0.448  ±0.007 (+0.441..+0.455) 
Double/Take:  +0.419 (0.029)  ±0.010 (+0.409..+0.429) 
Double/Pass:  +1.000 (+0.552) 

Best Cube action: No double / Take 
Percentage of wrong pass needed to make the double decision right: 4.7% 
Rollout details 
1296 Games rolled with Variance Reduction. Moves: 3ply, cube decisions: XG Roller


Double Decision confidence:  100.0% 
Take Decision confidence:  100.0% 
Duration: 10 minutes 11 seconds 
eXtreme Gammon Version: 2.00
And here is a DMP RO:
1.  Rollout^{1}  8/3 8/2  eq: 0.135 
 Player: Opponent:  43.25% (G:3.82% B:0.06%) 56.75% (G:13.95% B:0.78%)  Conf.: ± 0.004 (0.139...0.131)  [100.0%] Duration: 3 minutes 45 seconds 

2.  Rollout^{1}  16/5  eq: 0.189 (0.054) 
 Player: Opponent:  40.57% (G:3.35% B:0.03%) 59.43% (G:11.07% B:0.77%)  Conf.: ± 0.003 (0.192...0.185)  [0.0%] Duration: 4 minutes 20 seconds 

3.  3ply  16/11 16/10  eq: 0.306 (0.171) 
 Player: Opponent:  34.72% (G:3.28% B:0.04%) 65.28% (G:19.11% B:0.57%)  

4.  3ply  8/2 6/1  eq: 0.369 (0.234) 
 Player: Opponent:  31.55% (G:2.40% B:0.02%) 68.45% (G:24.46% B:0.65%)  

5.  3ply  13/2  eq: 0.420 (0.285) 
 Player: Opponent:  28.99% (G:3.50% B:0.05%) 71.01% (G:22.05% B:0.64%)  


^{1} 1296 Games rolled with Variance Reduction. Moves: 3ply, cube decisions: XG Roller

eXtreme Gammon Version: 2.00, MET: Kazaross XG2