Hi, the correct move seems a little risky. I’ll almost certainly get hit and it could easily be game over from there. I went on to win the game with my safer/more cautious move

It'll help to think more precisely about the hit chances. It's only a 23/36 chance of getting hit after the right play including 44 which hits on Blue's side of the board. So it's a big mistake to equate this to "almost certainly." After the safer play, it's 19/36 including numbers that hit on Blue's side of the board. So it's not that many more nominal shots to hit twice.

The hits on Blue's side of the board tend to be less effective, but after the right play, some of the hits like 36 aren't that effective either since Blue will still have one on the bar, so you're not doing too bad there. Meanwhile, if you get away with it, hitting twice is far and away better.

Ok, thanks for the analysis. I guess it falls into the category of brave move to make in the heat of battle/not quite as risky as it may seem but the payoff (if you get away with it) puts you in a much stronger position.

You simply MUST double hit here. I know you won after the “safe” play, but honestly that was lucky. Your blot on blue’s 5 point is key to you having any chance in this game. He will play very aggressively and hit loose on the 5 if you give him the chance. If he knocks you off the 5 point and makes the full prime or closes you out before you can anchor or escape, you are pretty much dead, and may lose gammon as well. If you anchor first or escape, you have reasonable chances and likely will not be gammoned. After your double hit, he may hit one or both of your rear checkers. If he does that gives you a chance to anchor. If he misses, that gives you a chance to escape. Giving him half a roll makes it much less likely that you can do either.

Hi
I want to show you this position:

Black: 2 point (2 checkers), 6 (5), 7 (3), 8 (3), 13 (2);
White: 9 point (2 checkers), 14 (1), 16 (1), 17 (2), 18 (2), 19 (2), 20 (2), 21 (2), 22 (1);
Black to play: 4-1
Cube: 1

Black 105 pip, White 115 pip. The correct move according to XG is 8/4 2/1. The move 8/4 is easy, but why 2/1?. The 6/5 move looks reasonable, but it is actually a mistake, other choices are blunders.
Do you have any substantive explanation and conclusions?
Thanks!

XG is wrong there. What's happening is if Black play 8/4 2/1, it tricks White into running off the point in Black's outfield incorrectly with a number like 64 and so that artificially increases the equity of 8/4 2/1. XG will keep the point correctly on a deep evaluation, but not on the low plies which it's using for it's lookahead:

Thank you for your solution!