Moon
Knowing all what we know about DD, what do you think will be his approach? He's very methodical. He identifies needs, then goes about resolving them (within reason of course).
IF we win it all, will there be a grace period to be patient and wait as we solve internally some of our shortcomings? Acquiring a Ziegler type reliever(s) should not be a big issue. Picking up Clay B's option will be the easiest way to assure some depth for next year.
I suppose he may chose to wait and see for trade deadline and react to what we need. I always attempt to look through management's perspective. I'm just not sure what the limits are with player payroll.
I did read something to the effect, for the Yankees anyway, it was additional $30M or so when they make the playoffs versus not making it. And most of it hits the bottom line because player salaries are fixed.