From 2000 until the first quad tear Triple H was the best in the business IMO, and despite all of the Flair jokes we make about him he really was a modern Flair at that point in that he was a heel champion that could carry the show.
I also don't have the issues over the "Reign of terror" that many do as I don't think WWE had a guy that could pick up the slack, I certainly don't think RVD or Kane could have, and they tried Benoit and Goldberg to limited success. The other aspect is that the reign actually led to the creation of a new main event star in Batista, and it was done the right way, not with the 50/50 stuff, when the time came Batista beat him decisively 3 PPV's in a row.
Where Triple H lost me was 2006 when DX reformed, it was awful in every way and helped nobody. From there the 2nd quad tear saw his work take a bigger nosedive and he remained a face and his limited mobility and sagging in ring work sucked in that role, as did his character that was always a 100 times better as a heel. On top of that he damaged guys like Orton, Hardy and Punk over the following 5 years through his ego, at least as a heel there was some pay-off for those that worked with him.
This last few months is the most I've enjoyed him in 7 years and even then I don't really care about seeing him wrestle again, however I do believe that if he puts over someone like Bryan, Cody or Sheamus at Mania then him getting back in the ring for the pay-off of this angle will be worth it.
I've always thought Triple H was better than The Rock in every year they existed in the company together apart from 1998.