Its just my opinion, but I'd be surprised if he makes it. Of course its certainly not out of the question, but personally I'd give him a 10% chance.
Have to admit, this made me laugh and nothing more. 10% is folly at best.
Another negative is he doesn't have a ton of power. A lot of the 3000 club are able to maintain their careers because even if the batting avg suffers, they still have some pop. This won't be the case for Jeter, he'll need to continue to stay a .300 hitter throughout his career. (which, in retrospect, severely damages Juan Pierre's chances)
To further poke holes in your theory, a lot of the 3000 hit club had power? Interesting...Pete Rose
Ty Cobb
Tris Speaker
Cap Anson
Honus Wagner
Paul Molitor
Eddie Collins
I only listed seven players of the top 10 on the all-time most hits list as the other three (Musial, Aaron and Yastrzemski) had power. Did these guys have a lot of power? Among all seven combined, there were TWO 20 homer seasons.