I've been thinking about this actually. And don;t get me wrong, I don't want Shawn to retire at all, but it'd be stupid for someone to think that this isn't on his mind if not everyone elses. He isn't in the same physical condition as he has been. and even though that doesn't make much difference to us as the fans as he is still brilliant in the ring, it makes a lot of difference to Shawn Michaels, as he's the one who feels the pain and tiredness that many other people don't understand.
With your suggestion, the one thing I don't understand is him winning the belt the day he retires, I find this pointless. However what I wouldn't fnd pointless is him having a championship run in his final year of wresling, or at least some time before he retires. I don't think many would disagree with the fact he deserves it, and definately deserves more runs than the amount he has been given.
I think Shawn, unlike Ric, should win his last match. the storyline with Flair was good, for him. However I don't think it'd work with Shawn. I think he should set a date, e.g. a Wrestlemania, and tell the world that will be his last match, regardless of win or lose. Him losing the match wouldn't be a bad thing, or a bad reflection of his career, as it certainly wasn't for Flair, however due to the nature of his gimmick of going out compared to Flairs, Shawn should win.
When trying to determine who should be the person to end his career, I think it's safe to say very few people have earned that honour. With Ric Flair, they chose a brilliant superstar to end his career, someone who always has great matches, and who had definately earned that. Out of respect for Flair, Shawn was one of few people who really should have been allowed to end the legacy. This is something Shawn Michaels also deserves. However, take Shawn out of the equation and who are we left with?
Triple H - Definately an option, and at the moment probably my favourite. The 2 have had such brilliant careers, and I'm a fan of HHH. Every WWE fan is familiar with the amount of history between the 2, whether it's love or hatred. Their matches have also always been brilliant. I love seeing them in the ring together, whether together or apart, as you just know you're going to see something special.
I'd never like to see them have another feud, as I think it's been done to the death and would definately take away from every other brilliant thing they've done in the ring. Fans should always remember the past matches they've had, as if they had anymore people would remember this feud for the many who would comaplin "We've seen it all before". However the one thing they haven't seen before is Triple H ending Shawn's career, in Shawns last ever match.
Hulk Hogan - The two had a good match a few years back, and Hogan definately has the fanbase to make this huge. However Shawn doesn't need that, and it'd be upsetting to see Shawn's career ended by this man. The 2 just don't compliment each others styles at all, and even though they can work together, I'd much rather see someone else who Shawn works with brilliantly.
Also, as I stated above, I want Shawn to win his final match. With the people we have at WWE, I think I can say quite easily that Shawn Michaels would not win if put against Hogan. Due to his 'hero' status with many fans, they would be unhappy with him losing, despite it being Shawn's match.
Austin/The Rock - I'm sure you know what I mean by classifying them together. They're both gone now, but still firm in the fans hearts, and still classed as big stars by the majority. Both have been the face of WWE, and everyone knows who they are, even the completely new fans.
Shawn and Austin had a great match before Shawn retired in 1998. Just imagine how much better it'd have been if Shawn wasn't on his way out due to an injury that bad? I think they could really have a good match, and I'd love to see it happen. However, same stands for with Hogan, would he come back to lose? He may do, but I can't see it as completely sure.
And also, a problem with bringing a wrestler such as The Rock, Austin or Hogan back for just that one night, is that the fact it's Shawn's last match would be taken away from. He deserves all attention to be on him, and every cheer to be for him and his career. I can't see it happening with these people returning.
Mr Kennedy - Has A LOT of potential at being huge. I think he's defiately going to be face of the comapny in a few years time. I think the odds on Kennedy ending his career are dependant on when Shawn does decide to retire. If it's Wrestlemania 25, I definately don't think he has a chance. However if it's closer to Wrestlemania 30, I could see him doing this. Not only would it further push his career in the right direction, it would also instantly give him a hall of fame name, if he wasn't aslready at that stage.
Whoever ends Shawn's career will automatically go down in history, as it would be one of the biggest things for someone to do. I also think it would fuel heel heat massively. I can't see many fans being happy with Shawn retiring, and if Shawn also lost his last match to this person, the crowd would turn on him like that. IT all depends on the direction they go in, but it would certaily be interesting.
As for type of match, I think in the end it should just be a regular singles match, no titles, no gimmicks, just Goodbye and Thank you Shawn. This way, nothing could take away from the skill we will see of Shawn that last time, and that we know he will deliver in massively, no matter his physical condition. He will be remembered for so much, that his last match will just be a tribute, yet the tip of the ice berg in what has been an amazing career.