He's being quite serious. Windows 7 Phone apps can easily ship with a trial mode, which, when activated, allows you to use the full app. This is in contrast to iOS applications, where the trial apps are inevitably their own, completely separate applications (e.g., Angry Birds Lite). On top of the annoyance of simply having two applications to deal with, the separate applications, plus iOS sandboxing rules, mean that data from the trial application cannot be transferred to the full application in most circumstances.
Gruber has actually been quite bullish on Windows 7 Phone, and I think he's being completely serious about this statement.
> On top of the annoyance of simply having two applications to deal with, the separate applications, plus iOS sandboxing rules, mean that data from the trial application cannot be transferred to the full application in most circumstances.
I could hack this using URL schemes within a couple hours, but admittedly it was not too much data (1kb? :)). I guess iCloud could make it even easier.
It still is a nightmare, usability wise. When you have an iPhone and iPad, iTunes is terrible enough even without application duplicates (Lite/Full and even HD sometimes).
Is he being ironic? I've never used a Windows Phone, so I can't tell.