DO IT!

You have been jabbering about "Cloud This" and "Cloud That" for years. Since you really don't have any medical, financial or legally sensitive information and SSC is a web site, not a critical business service set in a "real" enterprise, you should be a perfect candidate for Azure. Practice what you preach/pimp.

As for email, you need to tweak it anyway. I currently get two emails to the same email address, everyday. Figure this out, you might be able to reduce your emails. Also consider forcing people to renew/validate every couple of years.

As for confidence, that's not an cloud issue. The primary cloud issues are security, control and connectivity. Many of us and our clients can't legally use it, don't trust it in light of the NSA revelations, want more admin control and don't fully trust the US network providers not to screw us over...