It's a marketing thing. Everyone knew Yzerman's number was going up there, but the team waited to try and set up a meaningful day where they can make an event out of it and sell some extra tickets. The wait wasn't a sign that there was internal debate among the Red Wings staff, they were just trying to find the best day. The fact that Yzerman's number was retired his first year in the land of retirement shows that he was a given.
As far as Ozzie is concerned, 400 wins isn't enough anymore. Remember how the 80s were for assist and goal scorers? Well thats how the new millenium is for goaltender wins. Now that you have guys playing 70+ games per season, and posting high save percentages, you're going to have a lot of goalies eclipsing 3-400 wins. Osgood has had some memorable seasons, but that's about it. He has never a dominant goalie (and don't let 96 fool u, Detroit was unbeatable that year in every aspect, all Osgood had to do was not screw up bigtime). Winning only one Cup as a starter, and having 400+ wins, isn't enough for the HOF, especially if the majority of your career was in the stat-boosting Detroit system. Legace was 37-8-3 in 05-06, that's impressive if you're only looking at statistics too.