I've never done the full 15 year assessment, but, on average, the smart people throwing themselves into hosting my business applications have performed at, or above, any level that I ever could.
People always talk about down time from third parties, but always seem to forget how much downtime self-hosting induces - particularly as you usually can't afford the 24x7 well-staffed NOC and operations team.
The temptation is always to say "I can do it better myself" - but the reality is you probably can find someone out there who can do it better than you, and, even when you "Self Host" - 95% of the time that really means relying on someone else to provide you a data center with generators/diesel/hvac/security/Sonet/etc...
With that said - Fog Creek is a tiny little operation, that probably operates at, or below the level of our own Operations team - so it's a coin toss as to whether they would do better than us at hosting.
On the flip side - I'm pretty confident that gmail, on average, has had better uptime the last 10 years than the mail servers I've managed. (Though, the last 5 years have been remarkably stable for self hosted email. Exchange has come a long way...)
Given that this is a unpopular view around here anyway, I want to add another thought:
If your company has it's own webpage at datacenter A, including payment from datacenter/service B with CDN C and Twitter-integration D, using hosted FogBugz for support mails, hosting it's CSS-stylesheets on TRELLO which was baked by Google AppEngine, and using email provider E...
Why don't you have downtime at leas one a quarter???
How can a system that relies on so many components and other companies be reliable? With all those AWS-outtakes? I don' understand this.
If you host most of your stuff yourself, either everything works, or nothing. But not all goes down at the same time.
[1] https://www.webputty.net/ [2] https://github.com/fogcreek/webputty
However (regarding AppEngine based solutions), as far as I know, if AppEngine goes down, there is no way to have any backup, is it? Only google can host AppEngine apps.