deeg, I don't see it the same re Cobb/Chatwood.
1. Don't think that would preclude signing pretty interesting relievers, plural. IIRC, Jeff had us down around $120, maybe less; so $12 Chatwood, $14-15 Cobb, $8-each for a couple of relievers, could still have some room.
2. Also not sure that filling the rotation with $10/year guys would preclude going after a good playoff-starter next winter. With another year on his tired, Lester might be cooked by then. If everybody is healthy and Lester is still a desirable rotation guy, that's all great; moving Chatwood at $12 to relief seems no problem.
I do agree that a rotation of Q, Lester, Hendricks, Cobb, and Chatwood, none of those guys look like they're going to be advantage-pitchers in the playoffs. When facing Scherzer or Strasburg or Kershaw, are there any of the Cubs 5 (hypothetically including Cobb) where you'd feel our guy was better than theirs, or more talented? We're going to pitching from behind, talent-wise, in the playoffs, that's a given. But, what do you do? It's not like there are any Strasburg-like aces sitting out there being offered in exchange for Almora or Happ or Zobrist.
I also agree that bullpen must improve. I think that might be more true than ever in event of Chatwood+Cobb being added as 5+4 starters. Neither have history of injury-durable; neither have history of innings-eaters. Chatwood's control and 1st-2nd-3rd-time-through-order combined with Cobb having only finally passed 150 innings, that suggests to me that both guys shouldn't be asked for 7 innings very often, and you should build your bullpen well enough so that if Chatwood normally gives you 5 good innings and Cobb 6, you can pick up the other 4 and 3 innings routinely by your pen. That may be problematic if doing so means you're alway turning to Grimm or Maples or Koji or somebody of the Felix Pena/Florio caliber. Pen obviously needs good guys plural.