In case you missed it . . .
While I was taking Punisher apart and had the front cupholder in my hand, I decided to lube it and investigate improvements.
What I found was that by doing some judicious work with the Dremel, I got the cupholder working as it was designed. It pops out every time now.
As you can see in the pics, I found wear marks on the bottom side of the articulated arm. I removed some material and smoothed it out some. It works great now.