Red to play 64.

I don't think I'm seeing why upgrading the defensive anchor is important at all here, to be completely honest... pointing on his head seems pretty sound to me.

I run to the 14, but I'm not sure if I want to hit or not...

So you don't like making either point?

Making the 2 point strips all of your spares which will lead to awkwardness. I don't even think that putting white on the bar like that really increases your gammon chances because he's got the double anchor.

You're ahead in the race, so race! It's either making the bar point or running to the 14 point (I can't help but hit the checker -- it just seems wrong to pass on hitting the slotted 5 point). Making the bar point gives you the most comfortable timing to extract the last checker. I think I would favor the bar point because white isn't really in position to attack the lone blot and really be a big threat to your position, and I don't want to give white a 6th checker back and get a 2-3-4 backgame going. That just sounds like bad news.

This is not a question of "upgrading" your anchor.

You have a nice fourprime and you're way ahead in the race. The only thing that you can't allow to happen is that you get stuck with your back checkers. 24/18 22/18 starts moving two of your checkers while white has two blots in his board and really is in no position to attack.

Making the 2-point looks completely like the wrong gameplan. The spares should be used to attack white when he's (hopefully) forced to break one of his anchors down the road or handling awkward rolls later on. By making the 2-point you basically now have four checkers out of play, and you have some rolls that will force you to break your prime on the next roll (53, 55 or 33 would be a disaster for example).

This is actually a very instructive position IMO.

Most of the rest of the responders have made the key points, but I think it helps clarify things if you imagine removing all the blots. Because the blots ARE fundamentally irrelevant to the key challenge of the position. Unlike most positions, it's far from clear whether hitting even helps Hero here, because it often just lets Villain maintain his timing and his forward position.

So, with no blots, it's clear that making the 2-point is essentially useless and just leaves your position completely stripped. The key to the position is that you have to scramble 3 checkers out from behind a reasonably decent blocking position before your front position collapses and/or Villain seizes control of the outfield, and 24/18 22/18 is the best way to do that.

Thanks guys-- that all makes a ton of sense.