I still don't understand how a pitcher's value fundamentally changes during this period. There are so many things between now and then that can happen, it's mind-boggling: injuries, schedule changes, rainouts, double-headers, rest for the playoffs, extra starts in order to make the playoffs, etc.
I guess I don't see why Santana or any pitcher becomes more valuable. And I do understand that as the season goes on, good pitching becomes more valuable. I just don't see how you can 'time' the pitcher and increase his worth for the playoffs more than a month before that time.
Santana is the best pitcher in the league. Period. The only way I would part with him is 1) The other guy overpaid and 2) Made me an offer I couldn't refuse and 3) The offer made my team better.
If you are looking for more dependable pitching to go into that period, that I can understand. And you will have to pay more for it today than you did at the beginning of the season. But the teams faced during that time (as of today) should not have any effect on value that I can see.