Good discussion. I'm pretty comfortable letting Theo and those guys try to come to a decision. Too complex for me.
1. Conservative approach might be OK for competing for and perhaps winning the division.
2. To win the World Series, they might need to convert on a higher-ceiling guy? Or maybe not, maybe Lester-Quintana-Hendricks-Cobb would be a plausible WS-rotation, if you had really good hitting and pen...
3. A #5 guy won't be high-ceiling without either a high price or high risk or both; only affordable-and-limited-length if some serious wildness and injury risk.
I'd love to see Cubs sign Chatwood as #5. They wouldn't unless they had reason to believe he had a solid chance to be good outside of Coors, and thought he had a reasonable chance to throw enough strikes.
I'd also enjoy adding two strike-throwers. Hopefully the offense is consistent and relentless, and the defense plays at a high level so that guys don't need to be afraid to throw strikes, even if some hard contact results sometimes.
Nibble less than bullpen and Lester and Quintana did this year.
I guess my feeling is to go for a Cobb-like #4, who mostly throws strikes; and then take a riskier shot on #5. Like Chatwood. If he flops or gets hurt, it's not the end of the world and you can improvise. But if he did emerge, and improve his command, and stay healthy, maybe you've got a steal.
To some degree, if you're going to win the World Series, some things need to break your way. A risky guy works out; a guy doesn't get injured. Maybe somebody outperforms their contract.