This is a fun thread. I'm back again. I'll respond with short answers first and then long answers
@pat park
Yes, exactly! Silly is exactly how I would describe it. Even if I was an employee, I would still recommend owning an actual iTunes copy because you can now have access on iPads, iPods, Macs, Windows boxes (with iTunes installed), Apple TV, and iPhones. Not only this but if you ever have a corrupted copy, you can just redownload the content which is going to be higher quality than ripped content. Are you closing yourself off to the same system/ecosystem? Yes. But then again, you would have done it if you bought Blu-rays or DVDs or VHS cassettes. iTunes is specifically designed to play and manage content specifically for iDevices. It's just that simple. After investing in iTunes, you can also connect Android, Windows Phone, or most other products.
@balamw
I agree with the media statements. If people expect drag and drop, iTunes is perfect. If people expect to use other formats that aren't native to the systems, they should expect to understand the formats in order to convert them. The major issue with compatibility with Apple systems is due to copyright restrictions and legally binding anti-piracy standards. Apple seeks to make their systems piracy resistant and that's the true nature of this thread. "How do I pirate content for my iPad?" is the question here. It's not that Apple products are complicated or frustrating because most users in the world would really disagree with that statement.
@Sphinx99
There are 2 reasons why people can't use iTunes. The first is that they are unwilling to learn the system. For a completely novice user, it's pretty simple. Purchase songs on iTunes, create your playlists, sync to your device. It's 3 steps. For videos and TV shows, it's the same thing. Purchase videos on iTunes, sync to device. For books and apps, it's the same thing. Purchase apps and books on iTunes, sync to device. It's nothing tough to understand but people resist it like the plague because they just don't see it that way. I used to be one of those people. I used to think it was complicated because I managed an entire hierarchical file structure for my MP3s and FLACs. I did the same with video content such as MKVs, MP4s, M4Vs, AVIs, RMVBs, etc... What iTunes does is suppose that you are a complete slob. They ask you to just throw everything in that is compatible. That means MP3s, M4Vs, and MP4s can just be drag and dropped in. Everything else, iTunes views as incompatible because they will either affect battery life, performance, or have other potential problems with devices. This means you need to convert and then dump into iTunes. If you're having problems with these steps, Apple provides training at the Apple stores so you can understand how things work on Apple systems.
The 2nd reason why people can't use iTunes is due to their content. If you're working off of file formats that you originally had and some of it is protected like some CDs, DVDs, and Blu-rays (not sure about Blu-ray encryption now), you'll need to jettison that content and repurchase it in iTunes or convert fresh copies that aren't encrypted (most likely pirated). Anyone coming from this structure will hit a brick wall with iTunes. Most of these people use Windows and don't understand piracy, what they are downloading online, codecs/containers and how they are used, and they are also the people who order seafood in steakhouses in the middle of a continent. There's a disconnect between the user and the system because of the kind of content the user owns. If you are savvy enough to do the conversions and work past your existing media, you'll find a lot of value in the Apple ecosystem. If you can't work past this, you should not be buying ANY Apple device.
Regarding the Canon DSLR, I use a few myself and I've had no problems using iMovie on the iPad with the Camera Connector. It helps my workflow because I can start calculating how much footage I have and what is usable almost immediately after I take the footage. That is simply amazing from a photographer/videographer's viewpoint. The point is, MOVs that are going to go to the MBP, iMac, or MP can have the video imported from the iPad or you can import the movie directly on any of those and then start your laptop or desktop workflow. The MOVs are not natively supposed to sync via iTunes because anything you create on a laptop or desktop should be producing a finished MP4 before enjoying it on the iPad via videos. There's a separation between content creation and content consumption so then you're not mixing up your preliminary cuts with finished and complete videos. While a lot of Apple employees won't be able to tell you that, if you made an appointment with an Apple specialist or an Apple creative, they would be able to explain the iPad video workflow and how you can best function with it. A normal Apple store leader, most likely won't know what you're asking about because there are a lot of product lines and services.
Lastly, iTunes on Windows is a sore point for me because it's how I got started with Apple products. I used to be a cracker/genius or whatever you would call them. I used to hate it but now I can't live without it. There's a good reason why iTunes is inferior on Windows and why most of the calls into Applecare concentrate on Windows users. I guess the best place to start is a small history lesson. Back in January of 2001, Apple released iTunes. This was only available to macs back then so it had no bearing on my music usage. The Windows version was first available back in 2003 because of pressure from other Apple execs. They saw that it would make money due to iPods they would sell and they decided to do it. The cost to making iTunes Windows compatible was some of the back-end functionality that consumers would almost never see unless there were problems. iTunes for Windows originally had problem access the services in Windows as well as accessing the ports necessary for iPods to synchronize with iTunes. Digital signing issues, windows registry corruption issues, quicktime implementation in windows, and the isolation of it's file management system were some of the biggest problems that the Windows version faced. My first thought when I used iTunes was "Why is this thing taking up so much space?" This progressed to "Why is iTunes duplicating my music and content?" This then progressed to "Why can't I have folders?" Connectivity problems to iDevices and Windows Vista made me convert to Macs. I then understood why iTunes works the way it does. It assumes I'm a slob and can't organize music myself. As time progressed, this proved true and I realized that I'm expending a lot of effort for something that should be easy. I then figured out that I can just mass dump everything into iTunes and it would sort it all out for me with custom playlists, smart playlist which will pull out a specific artist, style, or album or combination of those. Movie files, when formatted correctly played more smoothly than most other content out there at less processor cycles. I then started seeing that iTunes could be a hub for all of this content and I didn't have to keep up a good hierarchy of folders because it did everything for me in one database that was instantly searchable. Overall, the basics work better on a Mac because iTunes was created for Mac originally.