Well custom channel letters need holes in less predictable spots, drawing holes on the pattern is less useful than a cross, since if you rip the center away on a cross, you can visualize center, but on a circle it's...less easy, especially if you make 1/8" holes and the drill skitters across the pattern and that hole is now ripped off and bunched up. Making the file for the letter you need circles, then at some point you need to generate the pattern, so now X's. Yes I should have a library of hole sizes with X's centered on them and place them all at once. Do I? Nope. At least now I feel even dumber for not having one so I may just get started on it.
You game sounds legit, as long as your customer base drinks the koolaid and lets you set the rules. We just waste and price out accordingly, though I be my competition would sell 3 32" panels from a sheet as 3 3' panels and not tell the customer up front. I always like to give the option, and most folks take it, especially my construction guys ordering coroplast. "I need 7 3x3's" "no you don't, why don't I sell you 16 2'x2's for less?"
For me nesting is to tetris, where you're stacking blocks. Just that nesting implies different sizes/shapes/orientations(trans squares and the like)/etc