Ok so here's how I feel. Triple H is a WWE legend. No denying it. As mentioned, dude was one of the top heels in the business. Was an important bad guy to a lot of our favorites. Had some good matches and feuds here and there. I won't discredit that. Behind the scenes, the internal success of NXT is driven by him. He's making some good decisions for projects not run by Vince. We get that. (speaking of NXT. That whole deal with him coming out and raising Cedrics arm was more of him trying to speed up the show. I don't think he was trying to take his spotlight. Still should have let him have his moment though)
With that said he has a ton of questionable moments. There is no denying that his RAW run went way overboard and he took power to his head. I won't go so far as to say he wouldn't be anywhere had he not married into the family because he had a nice track record prior to all of that. But I will say that marrying into the family enabled his power and mindset for those long dark periods of his reign. Again, some good came out of all that ( put Cena, Benoit, Batista etc over) but still.
I do think he was a little jealous of bigger stars in his heyday and tried to manufacture his way into God like status. That explains his heavy run on RAW when Rock Austin etc were gone. Its why like post 2002, he doesn't really cut it as a believable baby face. Even in later years with HHH going over Punk in 2011 during his rise and getting win backs from Brock. Some stuff just needed to be left alone and that hurts HHH rep in a lot of people's eyes. So it's like with every good HHH will do (put over Bryan or Roman) he'll go and do something questionable to strike his ego.
Anyway when he does fade out for good and years will settle he'll be remembered as a guy who played his heel role well. With some good matches and feuds. But made a lot of power play moves. Kind of like Hogan.