That said, with Milwaukee, Pittsburgh and Cincinnati, this division will always probably be pretty bad. All three of those teams may put together some shorter runs and nice years now and again, but given the factors you listed it will be tough to sustain long-term success - unless a Billy Beane-esque figure arises.
Exactly, they counterbalance the Cubs (and somewhat the Astros) the Astros are like the Reds in one way, they share their Fox Network with a AL team, no big feeder like WGN for them. When looking at what is a monster market only Chicago stands out, St Louis stands out as how a smaller market but with less regional competition should do it. (Colorado and Arizona should look at the Cards to build their surrounding fan base.