Approaching 30 years, 2010 (assuming he wins) will be his sixth term.
I don't think Specter is going to win. The unions and Dems that normally cross-over to support him are going to vote for whoever runs as a Democrat. Toomey has his work cut out for him, but I think his small-government and fiscal responsibility message will play well in PA. GOP needs to stay out of this race though. Cornyn is an idiot for doing this.
He's well on his way to achieving that goal, since Peg Luksik, Larry Murphy, and Pat Toomey are all announced primary challengers to Specter, and all three can point to very solid conservative credentials. Specter expects to win the same way Topinka was nominated for Governor and Bob Corker was nominated for the Senate in 2006. Both were RINOs who won with less than 50% of the vote thanks to the conservative majority in the primary being divided.
On election night, we might likely see something like this in Pennsylvania :
U.S. SENATOR - REPUBLICAN PRIMARY
Arlen Specter 40%
Pat Toomey 38%
Peg Lugsik 17%
Larry Murphy 5%