Others have made excellent comments on this particular position. Here I will just add a couple of extra general comments.
1. If you're trying to understand a subtle checker play, first switch to money play or a normal match score and try to understand what's going on there. Then go back to your original match score and see if there is a difference. This will help you sort out general principles from the peculiarities of that particular match score.
2. Once you think you have a theory about what's going on, vary the position to test the theory. Here, for example, you might read the comments people have posted about your position and hastily conclude that in general it's better to step out, because getting pointed on in the home board, or even getting hit loose in the home board, is much worse than getting pointed on/hit loose in the outer board. However, consider the position below.
| gnubg | 157 |
|---|---|
| |
| tchow | 128 |
Position ID: mp1EgDHGzTEDQA Match ID: cIkRAFAAAAAA | |
Here the choice is more difficult than in your original position. An important difference is that White has a weaker board and in particular has a blot in the home table. If you play bar/21 8/5 here, then White is going to be more reluctant to hit you loose because you will then get a double shot from the bar. This variant position highlights one of the advantages of staying inside the homeboard: If you get hit loose, you'll typically have more return shots.
So the more nuanced lesson to be drawn is that you have assess the quality of White's shots as well as the quantity. How willing will White be to hit you in either case and what compensation will you get? Will White have to sacrifice an asset to hit you? Will you be totally up the creek if you get hit or will you still be O.K.? Unfortunately in tactical positions like this you are forced to go through all of White's rolls if you want to get a reliable answer. But if you know that you need to look at the quality of the shots and not just the quantity then at least you'll be spending your time gathering the right kind of information to make your decision.