Scenario 1: it is the opening. I have split to the opponent's five point. With my next roll I get the chance to either make the five point or run the checker on it to the midpoint. Do I always make? Do I always run? It would be different in a cash game as opposed to a match? The last time this came up it was in a 3pt match and I made the five point. However, if it was DMP or I was one away running would be better, right? Genuinely confused in this scenario.

Scenario 2: I have a sole backmen left in the opponent's homeboard. He has a four point board but no spares to hit. Usually, this man is run out into opponent's outfield so that it cannot be pointed on. But with no spares attacking the back man, it is best to just leave it unless I can run all the way to the midpoint, yes?

Many thanks in advance.

I think the answer is "it depends."

It depends on what your opponent rolled and what he did with it. If he rolled a big number, then you're probably behind in the race, and therefore you shouldn't race.

I think it also depends on what you can do with your 3. If you have a constructive 3 somewhere (perhaps your opponent has not yet split his back checkers and you want to have a builder), then you can do two good things by making a strong anchor and developing your structure. But if such a 3 is dangerous (your opponent has split), then maybe you should probably not be as loose.

Usually, yes. If it's getting late in the game, you might need to run simply because waiting hurts more than it helps. But if your opponent has no spares, I don't think you'll be in that spot.

Aaron, where does that 3 come from? Did OP ever mention any 3?

How else could you have split to the opponent's 5 point and roll something where you have the option of making the point or running to the midpoint? I think only 43 can work (unless I'm missing something obvious).

"Yeah but..."

Very good point.