I would think Ruben may still see broadcasting as a path back to the front office or dugout. But it's also a much easier life.
And yeah, hard to check off every one of the boxes, but lots of guys check off most of them. Even Kapler has done most of those jobs (never a GM, but Ruben's also never managed). Bat boy is probably the hardest one! I guess Dusty Baker's kid might be on track for a few more categories.