Took about 10 hours with many stop/start/wait/error/start/etc. to get to iOS 5. My impressions...
() Apple failed miserably to prepare for and deal with the avalanche of people trying to update several very different devices. A staggered process would have been a far better approach and would have avoided a PR disaster.
() I'm beginning to suspect that in addition to the demand placed on the Apple servers, the problems may well have been correlated with the amount of data on devices that had to be restored in the process. In my case I have an iPad 2 64G with about 35 gigabytes of data. Apple's estimate (displayed on my screen when the process began the first time) was that the update might be "an hour". That turned out to be an absurd underestimate even if the update had gone smoothly. But presenting an overly optimistic (to say the least) estimate to a user only fueled anxiety and a belief that the update process had failed.
() All in all, I suspect that apart from luck of the draw, those who were updating an iPhone with a few songs or an iPad with a few apps may well have managed to get through the process without difficulty and without the entire process timing out. I'm guessing that the way the algorithms were set for the update placed those with large restoration needs at a distinct disadvantage, a disadvantage that grew the longer the process took.
() The fact that the iOS update required an update of iTunes only added to the confusion and difficulty. I happened to have updated iTunes several days before but apparently because I have only an iPad and no iPhone or other "mobile device" associated with the iTunes application on the computer I use for the iPad, the updated version of iTunes continues to throw an error and tries to "fix" itself. Though this apparently had no impact on the iOS 5 update for my iPad, it only added to the confusion of trying to accomplish the update. And as I understand it, if I had been using a Mac as the computer for the update I would have had to have updated that operating system, as well. Piling one update on top of another for multiple devices contributed, I'm sure, to the entire fiasco and demand on Apple's servers.
So, bottom line...
() Failure to implement a staggered update process was a huge error for which there is no excuse. The entire process smacks of amateurism.
() Misleading estimates, uninformative error messages, and the usual terrible messaging in iTunes, (e.g. restoration will delete everything on your device) added to the mess.
() Apple's silence about the mess, the failure to provide a comprehensive iOS 5 upgrade FAQ, and the attempt to cram multiple updates to multiple devices and software applications into a complicated overall experience that does no credit to the firm.