Maybe it's as simple as us disagreeing, but as I laid out in the OP, the "now" timing would be to sell as high as possible & capitalize on the prized service time. Naturally it downgrades the positional side of the MLB club in the short term, but as is probably evident from other posts, I wouldn't manage the MLB roster/organization in the same way that Melvin & Co. do. If you're netting an elite-talent-tier SP under team control for 5+ seasons, the team could be even a bit better than it is today.