No one has responded, so I don't feel bad about a bot-assisted post here --

Unsurprisingly, XG++ says there's a lot more incentive to anchor up in position 1, as White's board is stronger and the checker on the 24 is more trapped. So it prefers 24/20 3/2 a little bit over 24/20 8/7. And by a lot over any play that doesn't anchor.

In position 2, anchoring is obviously less of a priority. I would have made the 2 point, but XG++ prefers 20/19 8/4 by .031. You do provoke a little more contact (for instance, White can't put a checker on his 12 point) and there is more duplication after moving up to the 19 point. Also it's better for disengagement. So I can see it.

Black should consider doubling before the roll in position 2. XG++ does think it's a tiny double, though a rollout may make it a bigger one. Seems like a good double in practice anyways, as I can see passing as White.