Tito makes it easy to dislike him and doesn't have the most convincing string of recent fights, but you have to remeber that his only recent losses are to the #1 and #2 in the LHW division. Sure he wasn't convincing against Forrest (or Vitor for that matter), but he did win, and both of those opponents are tough to pin down for where they fit in the division... on a good night they could both be strong contenders.
After watching TUF3, my opinion on Shamrock and Ortiz as people has changed a bit... and I'm not sure if I like either one now.
Other than his age, I think Ken's most obvious weakness is that he is no longer growing as a fighter. His approach is to use the same old tools while adding more determination and conditioning. Compare that to Forrest, who completely reinvented himself for the Tito fight. For that reason I don't see a different outcome in this fight.
In my opinion, this fight holds no career signficance for Ken - he just wants a chance to beat the hell out of Tito, and get a payday while he's doing it.
Tito, on the other hand, is walking a tightrope back into title contention and could be completely derailed by a loss. He has everything to lose and nothing to gain but a check. He's the next most obvious match for Chuck after Babalou (Chuck will basically be rehashing folks he's already beat this year), and coming off of the TUF3 show his marketability is high once again.
I should at least be an interesting fight, and I think Ken will have more success than Gracie did against Hughes. Who knows... with a Shamrock loss maybe Gracie's next fight could be against him (just kidding).