2 thoughts.
Regarding Big Woo. It never fails to interest me how multiple times he & the front office seem to both just relax and trust each other. He's hurt and a free agent, and it is a ways into the off season, what is he doing and where is he going, oh, he just signed a 2 year deal with the Crew. And now they give him a huge QO - likely because they talked and knew he was going to take it ... and trusted each other. I personally think they even know the next step with him, contact-wise. Have just consistently been amazed by that.
And regarding the pitching staff, it makes a lot of sense how you laid it out. 6 man rotation (or 5 1/2, with Freddy starting on a bit more regular pattern, perhaps). Some younger guys available in AAA. Similar pen. I do think they will cast around in March for another undervalued FA starter, and likely a AAA pen guy, just as good value options.
They are getting to the point, with the prospect depth, that they may not be forced to chase outside the system. That is a great thing. And due to the cost of the prospects, I'm sure the FO thinks so too.