IMO, right now Osgood and MAF are pretty much neck and neck in the HOVG tier just below the HHOF. And again, the following is all my opinion
Both guys were seen more as "passengers" on talented teams, and were clearly a level behind the best goalies of their respective eras. It's also interesting because both left their only longtime teams in a "draft" and then delivered better than expected results for their new teams.
MAF currently has a similar regular season record, but with better goalie related numbers. That said, Osgood get dragged down a bit by poor play after he turned 36. MAF gets the edge though in that save for his first couple years and his last season with the Pens, he was always viewed as the clear #1. Osgood on the other hand, went through various ups and downs where he was a backup or used in a tandem.
For now, Osgood has a decent edge when it comes to the playoffs. Won 2 out of 3 SCF as a starter, while Fleury is at 1 out of 3. While there were some years where Osgood could've been better in the playoffs, he doesn't have anything resembling the brutal looking stretch MAF put up from 2010-2013. As far as "clean" (where the goalie got all 4 wins) series wins, Fluery has 14, and Osgood has 13. Outside of those, each goalie contributed wins to two other series won. However, Osgoods were 1 series he one 2 and then got injured with Mike Vernon getting #3 and #4, and then getting put in place of a struggling Hasek and getting wins #3 and #4. Fleury on the other hand has one series win where he gets two wins and then gets replaced by Vokoun for the rest of the series, and then a series win where he had 1 win and then gets replaced by Murray, who would've been the starter anyway had it not been for an injury. MAF gets a slight edge in that save for his last season with the Pens, he always entered the playoffs as his teams clear #1 goalie, while Osgood started on the bench in favor of Essensa, Vernon, Legace and Hasek at various points in his career, and of course, when he was a clear #2 to Jimmy Howard for most of his last 2 seasons.
As far as All Star games, they're pretty much tied. Osgood was named to three, but missed one due to injury. Fleury has been named to and played in three.
Osgood probably has a slight edge in "team success". He contributed to 9 (not counting his last season) division winning teams, 6 conference winning teams, and 4 Presidents trophy winners. MAF has contributed to 4 division titles, 2 conference wins, but 0 Pres. trophies. That said, MAF was the clear #1 for all of those, while Osgood was in a #1A/#1B tandem with various guys for some of his, possibly #2.
Osgood also gets an edge in post season hardware/awards. He shared 2 Jennings trophies and was a 2nd team All-Star once. Osgood also has a 2nd place Vezina finish and more 1st and 2nd place votes for both Vezina and All Star. Fleury has no awards, with a highest Vezina finish of 5th, and a highest AS of 4th, both coming this past season. That said, most of Osgood's votes and his awards came in a couple of real peaky seasons (95-96 and 07-08), while other than 17-18, Fleury consistently garnered AS votes from 2011 to 2016 and had a 9th place Hart finish in 2011.
Fleury has the distinction in where he's had Stanley Cup and almost Stanley Cup success with two different teams, while Osgood made the playoffs outside of Detroit, but never won a series with the Islanders or Blues.
I don't think Osgood gets out of the HOVG, but his HOF conversation is more than his "400 winzz". Guy is top 10 in some all time playoff# categories, and his regular season wins were in the top at the time he retired.
I think if Fleury retired right now, he wouldn't get in the HOF.
For the rest of his career: I've often argued that if you took CuJo's regular season success and coupled it with Osgood playoffs and Cups, you'd have an easy HOF goalie. So I think if Fleury has another good 3 or so seasons as a #1 goalie, he probably has a much better chance than Osgood. Another Cup however (especially with Vegas), and he's likely in the HOF.