Hah, I know Ferris Bueller, so I get the joke, don't worry, I just thought it seemed redundant after the first one.
I agree that it's way easier to get an app running in the Simulator with iOS development, but to actually test apps on a device, and publish to the App Store, it's an awful process. Apple's been working to improve it a lot in the past year, but it's still pretty painful.
To be honest I think RIM is just trying to make a giant transition. Keep in mind that all the Playbook stuff came from QNX, so I imagine it's a bit of a nightmare merging it all that stuff into RIM's bizarre system. There's a ton of room for improvement, but it actually works quite well once you get it all set up. I think that was part of the idea with the free Playbook offer, trying to make up the gap between themselves and Apple/Google.
RIM's also tapping into the unloved but massive group of Flash Developers out there. You're gonna see a ton of apps from developers that haven't made apps before. These are developers for whom the App Store really isn't an option. A ton of the apps will be total crap (just like on the App Store), but there'll be some gems too. Having used the device myself, I can safely say that the hardware and the OS are solid, and so if the apps are good too, RIM will be doing very well, and the process will only get better.