Problem is you have a lot of downright losers as the most vocal people making those decisions. Burke - loser (outside of one Cup, thanks to Giguere, et al). Poile - loser. Laviolette - loser (at least recently). Waddell - loser.
Only winners in the room are Bylsma and Shero, who seemingly just wanted to bring guys they knew, like Paul effing Martin on the team, as if that makes any sense, and Orpik. And Lombardi, who simply kept making a case for Jack Johnson and Yandle, neither of which they ended up bringing on.
If you keep saying you want the "three best goalies," you don't choose Howard this season. It's as simple as that. You could make the same case for Quick this season. Why isn't Bishop there, as he has far and away the best stats of an American NHL goaltender?
As other have said, Callahan, Stepan, and Brown don't make the team if they weren't in big markets. They're all three having rather poor seasons, comparatively.
Just the good ole boys making decisions, as usual.