Derek Jeter is signed through 2010, but Joel Sherman of the New York Post says "Yankee officials already talk privately about dreading" the expiration of his contract. He lists all kinds of complications: Jeter's position, his salary, his declining offense, and his drive toward 3,000 hits. River Ave. Blues, IATMS, and others took on the issue recently as well.
We can rule out the infield corners for Jeter, with Mark Teixeira signed through 2016 and Alex Rodriguez through 2017. Assuming you're not comfortable with a 36 year-old Jeter manning shortstop, the options would be second base or the outfield. Robinson Cano's contract runs through 2011 with club options for '12 and '13. The Yankees have two full seasons to determine Cano's future in the organization. If he stays, can he play a better center field than Jeter, opening up second base? Is the experiment even worth it? Another inefficient option would be to try Jeter in an outfield corner.
If Jeter wasn't an icon, the best baseball decision would be to let him go after his contract expires. Since he is, we'll be debating this for the next two years. By the way, Jose Reyes and Jimmy Rollins can both be free-agent eligible after the 2011 season, if their teams exercise their 2010 options.