Cause what I usually do is to grab custom transform from a face, edge or simple another object and use it right after to rotate/move/scale around that
I'm pretty sure a lot of people use it in that way. Align to view could be useful but this one is much more needed.
What do u mean by edit the Redo Panel?
Thanks.

Still happening in 2.83 Alpha.
Is so annoying cause I use the brush all the time, I completely got used to it already :/

U could reproduce it by assigning a shortcut to the pose brush and execute it after doing a few strokes in the mesh with a different brush.
When u accede to the pose brush through that shortcut is when it will crash, it won't if u select it from the UI.
It's been happening since 2 2.82 Alpha builds ago. (9th and 8th) 7th seems OK.