I'll always remember Bill Robertie's concept of counting the good things a move accomplishes and playing the one that accomplishes the most.
Making your five does
- Making your 5-point
- Start your prime
- Gain ground in the race
- Put him on the bar so an unlucky sequence let's you double him out
All moves gain ground in the race, because it's 44 after all, but putting him on the bar without any major disadvantage gains even more ground.
And while making your opponent's 5-point is very good it also gives the oppenent the chance to make yours next roll, because you are not pressuring him.