Today I learned an important lesson

And that's the difference between Delete All By Type > History and Delete All By Type > Non-Deformer History and what it means to and does to your rig. One option deletes your modeling history, the other sodomizes your rig. Normally I'm pretty good about iterating saves and testing out major changes but yesterday that wasn't the case. I pushed the sodomize rig button, didn't test out any of the changes, saved, closed the program and today I discovered I lost about half a days work when I showed a friend what I was working on.

Well, I'll never make that mistake again.

Also I'd like to add that the Smooth Brush in the Paint Skin Weights Tool is a terrible, terrible tool. Even if I remove Joints influence from a particular piece of geometry, like how the ankle Joints have no business influencing the pants, or if I lock/hold the Joints in the Paint Skin Weight Tool option the Smooth Brush STILL adds value anomalies and gives me this ridiculous deformations that simply should not be happening. The Smooth Brush doesn't logically spread the value between the only two unlocked/unheld Joints that should be influencing the geometry it gives value to random joints in the hierarchy. I've spent so much time trying to make Smooth Brush not suck, I could have spent the same time just manually painting in the values with the Replace Brush, which is what I'm going to do now. I'll manually paint in the values on one side and mirror everything.