Weight paint by poseing and moving verts?

So I have my bones in place and the right arm skinned. (ish).

When the arm bends down, it makes a nice curve, but if I raise the arm up too high, I get a very nasty v shape pinch.

Is there a way for me to set a pose and then adjust the verts so that I can more easily control how the mesh deforms?
IE: An override to have faces contract when I move the bone one way and expand when I move it another or move toward and away from a shape that is different from the default mesh once the bone hits a certain rotation/position.

Here is the file:
GB man tutorial1.blend (1.32 MB)

Well yes, you can create shape keys and move the verts where you want them, and then connect that shape key to a driver based off the bone’s rotation, but…

You shouldn’t do that.

You need to take some time and learn about topology. The gingerbread man you have will never work for anything. It’s way too dense (too many verts) and there’s triangles all over the place. Simplify, and use quads (faces with 4 sides only) almost always.

Here’s a much simplified version of the gingerbread man, and this one will deform smoothly. Take a look at how he’s made and look through the modifiers.
GB man tutorial1-mod.blend (1.34 MB)

Ah, so that is why edge flow in topology is so important. All of the tutorials that I have gone through so far say that using triangles will mess up the topology and that its only bad because it would result in you not being able to quickly select edges (and really didn’t state any other reasons)

But those tutorials have yet to go into any dept as to why poor topology was a bad thing and what bad topology could break. <— Seeing it now, I would think that most tutorials would go over this before you even started to model.

90% of the models you make will use the sub surf modifier, and subsurf works very well with quads as it can sub divide them into four equal quads. Tris don’t work well it, and you will get bad shading artifacts. All quad meshes will also deform better. There is a kind of sweet spot in terms of mesh density for deforming, but if you have too many vertices you will get pinched deformations (like your first model)

makes sense