Compliments to the OP. This is an excellent thread topic.
I started watching and became a fan in 1996 after my cousin took me to see my first live event in Richmond, VA. It was a WWF house show. I was hooked from then on and haven't looked back. My viewership of the WWE has lessened a tremendous deal over the years, as the product has been on a steady decline ever since the start of the Brand Division/the horrific mismanagement of the Invasion. Once those dark days hit, I started searching for alternatives and that was when I became a serious historian of the business as a whole and got into watching the older stuff from the other promotions during the territory days on tape. I also found other current promotions to watch and go see on the independent circuit. Finally, the likes of ROH and TNA arrived.
As for the WWE, I stopped watching for the first time around '00-'01. Why? The McMahon-Helmsley Era/Power Trip (an era they are grievously repeating as we speak). It started when they did the angle where Austin got run over by the car in the parking garage (and it turned out to be Rikishi in what seemed like a last-minute storyline having nothing whatsoever to do with the Authority storyline of the day because even then WWE couldn't consciously book its way out of a paper bag).
With Austin gone and Triple H forcing himself into the main event scene and controlling everything and just basically ruining everything that had come before him...I stopped. I didn't watch again until Austin returned and put an end to the McMahon-Helmsley Era. Things just continued to get crazier after that, though.
I stopped watching again around '02-'05. The reason, again, was Triple H. He'd forced himself back on top, this time ripping off the Four Horsemen in the process with Evolution. Some consider it to be a damn fine era. I do not. Not by a long-shot. Mainly because we as a fanbase had only just recovered from one of the worst eras ever. There wasn't enough time between these long periods. Once they succeeded in grasping all the gold, I stopped watching. I tuned back in briefly when Goldberg showed up and was elated when he won the World Heavyweight Title away from Triple H. I tuned right back out a couple months later when Triple H won it back.
After that, despite some pretty awesome angles that went on during the next few years, I rarely watched between 2006 and 2013. The reason, for once, wasn't Triple H. I entered into some pretty crazy living situations where I didn't have any cable. I still kept tabs on it all via the internet (still do), and during the one-year period when I had cable back I watched religiously. However, in 2013, I cut it off for the last time when the current McMahon-Helmsley Era II began and haven't watched an episode since. It's still going on without any signs of stopping despite the need to have done so a long time ago.
You might have noticed a pattern there LOL. I don't outright hate Triple H. I do have some respect for him. After all, as Katt Williams would say, he followed the Pimp Manual right down to the letter. He's carved out quite a history for himself and he'll be remembered by many for it and one day I'm sure he'll book himself into the Hall of Fame.
It's just that he was so ridiculously and irritatingly selfish during those first five years that he kept himself on top. Every Raw was about him, two hours of Triple H every week. He almost never lost. There was never any real payoff, and that may be the biggest problem. A payoff is extremely important when it comes to super-heels and super-heel stories. You need that as a fan. A grand and glorious moment where the S.O.B. on the other side finally gets some five-star, knock-down, drag-out comeuppance.
That almost never happened for Triple H. Sure he lost a match once in an extremely rare blue moon, but there wasn't any real payoff because he always booked himself to look strongest even in loss. My other huge problem with him back in those days was that many a rising star was shattered to make Hunter look the way he made himself look. Many a great wrestler was booked into oblivion during those years. That man had a profound influence over the creative direction of the company and he used it only to put himself over...and over and over and over. Title reigns mean nothing when you give them to yourself.
Worst of all, he wasn't even that good to begin with. That's what pissed me off about the whole 'B+ Daniel Bryan' thing. Trips was NEVER that A+ guy. King of Kings? Please. He was just the guy who just so happened to be across the ring from Kings. You guys want to give Cena guff over his 5 moves of doom? Triple H only has three, if that. At least Cena has two different ways he can end a match. Don't get me wrong, I know he can cut a mean promo and yes, there've been moments where I was H's biggest fan - and all of those times, he was a babyface. But still...I know I'm not the only one.
Just one man's opinion, I guess. Rant over.