Oh, baby. i smell some good discussion coming.
I rated Kurt Angle as my #1 guy, so I will address that. First of all, Kurt Angle has the advantage of having wrestled virtually non-stop from all 10 years. Will that fact probably lead to an early death? Probably, but irrelevent. I've made it pretty well known that Angle has been too formulaic the last 4-5 years of the decade, but his first few years were some of the best years for anybody in modern wrestling history. From 2001 - 2003, I would argue that he was the best in the world, at LEAST in the US (except MAYBE Benoit, but I'm a mark). His 2000 and 2004 were also very, very great, though I'd say Rock was better in 2000 and Benoit was in 2004. As part of the Smackdown Six, one of the few good parts of the Invasion, and his Triangle with Triple H and Stephanie, I think he has a solid amount of good storylines to boast of for the first half of the decade.
His second half, dominated by his time in TNA, has not been as good. I would consider him "average" in terms of storyline materiel, with most angles being either extremely good or extremely bad. Where his position in the Angle Alliance/Christian Coalition storyline kept my attention, the mishandling of his feud with Joe turned me off of the product. Where the Main Event Mafia started off great, it eventually floundered into a mess. He has had some gems though--vs Jarrett, vs Lethal, vs Kaz, and his early stuff vs Styles. What I give Angle most credit for in his TNA run is a combination of (1) his willingness to take on the pressure of carrying a company, and (2) his willingness to put over younger guys. When you look at Shawn Michaels, he doesn't really fit into the first category and, without getting too into this never-ending debate, I would say that Angle fits better into the second category than either Triple H or Undertaker.
Shawn Michaels has obviously had a lot of fantastic work. Whenever he was in the title scene, it was memorable--vs Triple H, vs Cena, vs Orton, and vs Jericho. But I think it's worth pointing out that that was four title feuds. Triple H had to work with probably a dozen or more different title contenders. Angle got to work with Austin, Rock, Lesner, and Eddie, but he also had to work with Mark Henry, Hogan, and an unmotivated Booker T. When I was rating, I took in mind the quality of storylines, but also context. Michaels was working a lighter schedule, so he was not as prone to being stale, and he was able to work with a more diverse set of opponents.
I rated Shawn highly, but that's why I did not rate him as highly as Angle. I believe John Cena was my #3, and I stand by that firmly, and I actually thought I was being harsh by not giving him #1 or 2. Looking back at my list, I was obviously on an indy high, as I rated Styles, Punk, and Joe all in the top 10--a decision I might regret at this point.