IMO, the conversation has gone sideways. There is no moral high-ground like something is good or something is bad. It's more like any FA contract you sign. You can like it or not like it, but there will always be some signings that work out great and some that work out badly. Currently, imvho, we are way ahead on Raffy, ahead on RA, slightly ahead on Bello, well ahead on Whitlock, and behind on KC.
IRT to timing, imo, that's a 0-sum game. If you wait for 2 years, and the kid doesn't progress, smart move, you saved money. If the kid does progress, then bad move, you lost money. We didn't extend Abreu and lost money. We didn't extend Casas and saved money.