I wouldn't mind seeing this match. I'm sure it would be a good match with the only issue being it would be instantly overrated. Seriously, where the fuck did the obsession with the Iron Man match come from....
I'm a Ziggler fan but he doesn't deserve a match against Bryan. He'd wrestle Bryan and then go straight back to the mid-card. Pointless. Ironically, Ziggler doesn't steal all that many shows. Indeed a certain Roman Reigns has probably done just that more often than Ziggler despite his shorter career (being in The Shield did give him an unfair advantage.) If there is absolutely nothing else for Bryan than, sure, but I'm not convinced.
Ziggler should probably be in some sort of multi-man match for the IC belt. It's a shame MITB isn't around because he could have done a lot in that type of match. Him, Barrett, Ambrose, Harper, Sheamus for 10 minutes. It would work.
I'm not sure who Bryan faces. I don't think he should (or will) be in the main-event. There aren't many other options which is irritating. Sheamus would work and they would have a great match. Downside, however, is that it may be beneath Bryan and not entertaining/interesting enough to make it worthwhile.
I'd also consider fast-tracking Kevin Owens to the main-roster and have him work with Bryan at Mania. It would be a great way of introducing him to the main-roster and would give Bryan an actual purpose.