I count twice. He beat Taker to get it back and then got the belt from Yoko in 1993. Unless you are specifically narrowing it down to his run from 1984-1992, which is still really saying nothing as 1991 was his last full year with the company and we're at the end of November when he loses the belt to Taker.
I'd call Bret "rising in the ranks" an interesting narrative. It implies a form of meteoric rise occurred at this time where he suddenly surpassed or leveled up with the star players who were there in 1991. He didn't. There was a mass exodus of top talent leaving the company for months and he became the guy they took a chance on. He was considered a dependable talent and was certainly popular amongst the WWF hardcores but he was not super visible in terms of presentation. Nothing that happened in ten out of the twelve months in 1992 suggested some gradual build where Bret had become so red hot in the eyes of the fans and Vince himself that he was the defining choice to lead the company. He closed a major show in England because he was champion and they were putting a belt on the English guy he was working against. He had some excellent matches but the decision to have him run with the title was definitely eleventh hour. His match with Shawn was like fourth or fifth billed on the Survivor Series card before they had him win the title and he was not featured on the advanced poster for the PPV or the home video releases. By comparison, Undertaker and later, Ramon, had a far more organic "rising in the ranks".
Agreed and given the circumstances, it proved a wise move for all parties involved..
You're right about the Yoko win as I forgot that since that led nowhere but back to Yoko anyways. As you said, 1991 was Hogan's last full year. Hogan back then already hinted he wanted to be in Hollywood. One rumor that actually hit Toronto sports news was that the original plan was for Hogan to retire in LA in 1991(reason why it was originally in LA Coliseum), but due to sagging attendance since Warrior won the belt that got changed.
There was also talks on WM VI weekend in Toronto that Flair was in talks with Vince. I'm saying this to say that Hogan ending up having his last full year in 1991 was not surprising. Hogan was on borrowed time and the most hardcore smark knew it back then as it appeared in reports in sports news that use to cover wrestling then.
It is why Vince pushed hard to get new blood with Road Warriors and Kerry Von Erich in 1990 and then getting Sid in 1991. Ric Flair who was rumored in 1990 and even back in 1988 finally coming in was just icing on the cake. Ultimate Warrior was really suppose to be the heir apparent for Hogan.
In terms of Bret Hart, again from reports we were getting he was being approached from Flair to jump ship in 1989. The fans were gravitating to guys like HBK and Hart because of the excitement they would have in their tag matches. They broke up the teams knowing they would have possible new stars. Bret Hart also went solo fully in 1991 just as the talent pool was drying up that I mentioned. Kerry Von Erich didn't really pan out long term as expected when he went over Mr. Perfect at SummerSlam 90. Perfect ended up getting back the IC strap and then passed it onto to Bret at SummerSlam 1991.
The Legion Of Doom worked out even though the company really stretched them out in terms of how long they took to get the titles from The Nasty Boys at the same SummerSlam that Bret was crowned IC champ. Bret was the one who was relieved of the tag titles by the Nasty Boys before being the tag champ that LOD helped at SummerSlam 90.
I stated this on here already that by early 92 Bret again was being approached by WCW. There was fear by Vince that Bret was going to jump which is why he lost the IC title. He lost the title under dubious high fever in the storyline, but that was still to protect Hart from losing to The Mountie. Once Vince was sure Bret was not jumping he had Piper do the honors finally for Bret and obviously Piper was fine with that since he never jobbed by pinfall since 1984.
Bret Hart being put in the title match with Bulldog was not the original SummerSlam 1992 plan. The company was going to have the first ever ppv ladder match with Bret Hart and Shawn Michaels for the IC Title. So, Bret was going to be champion on that show regardless when it was originally scheduled for Washington DC.
I also stated before on here that Toronto Star had reported Bret thought he was main event worthy when he carried Bulldog in the last match to end the second biggest ppv of the year. It was reported by Norm DaCosta that Bret again threatened to jump ship if he wasn't going to be used in the main event scene. This was well known in Toronto press and Vince obliged weeks later with Bret as champion although that was not expected. I say this to counter what you are saying about Bret not being red hot or whatever.
The fact is Vince did not want to lose Bret Hart to WCW in 1992 with the way the business was changing and losing his stars like Hogan and so on. Bret filled a gap that was needed in 1992 and got put over by Piper and Flair who were big stars from the previous generation. Sure Bret did not get top billing at Survivor Series, but the guy who did get billing in Ultimate Warrior ended up leaving again. Vince had to get Mr. Perfect to come out of retirement.
For all intents and purposes, Vince was on the money to keep Bret from jumping since Flair, Savage, and Warrior were not around to main event Rumble or Mania. Savage I think Vince was wrong to bench, but that also shows Vince thought highly of Bret as now he probably thought he had his new Macho Man in the Hit Man. Bret Hart even made mention of this in his promo for WM 12 against HBK at the 3:04 mark in the video below.
Undertaker as champion then wouldn't work for what was talked about earlier in the thread by someone. Bret even talked about why it was awkward for Taker to be a contender then too.
As for Razor Ramone, I think we know the issues there with trying to put the company on his back to carry. He is not dependable as Bret.