With the kind of money he has to work with, quite frankly I'd expect more as a Yankees fan than just making the playoffs.
I'm sorry, the playoffs are NOT a crapshoot. Pitching is what wins in the playoffs and the Yankees haven't had a decent starting rotation for several years now which can be directly linked to the multiple first round flameouts. Point to the last several WS champions:
2007 - Red Sox - Beckett was disgusting, Schilling was great, Dice-K and Lester had clutch starts
2006 - Cardinals - Marquis, Suppan, etc. came out of nowhere to turn into Cy Young-calibre pitchers
2005 - White Sox - Dominant rotation from top to bottom
2004 - Red Sox - Schilling was terrific, Pedro was great, Lowe showed up big time
2003 - Marlins - Beckett's coming out party
Amazing what an 8-year WS drought does to a fanbase's standards