I am unsure where they statement that millions of users jail break iPhones and ipads if any thing it is the other way around. *At tops 10% to 20% may jail break the rest which is the masses that these devices appeal to donot jailbreak as they are more than happy with what they purchased and further more would not have a clue to understanding what jail-braking is all about. The same applies with other platforms like Android. In terms of Apple being out of touch with users I cannot understand that statement when iPod touch, iPhone series plus the iPads have been so successful. Your personal needs is what YOU want not what the rest of the world want that is in fact why alternative products exist. I sell Apples i series products including the ipad and not one person has asked why it does not have a direct USB port or why it does not have flash because they buy the product for what it is. I find also that customer satisfaction is the highest.
I do not and will not get into an argument with flash it is just a comment.
Regarding the OP's issue i can understand his frustration however that is why in fact products like Macbook Air etc exist. Maybe just may be Apple may support that type of need in future upgrades but for now it is one of the limitations but again for a small part of the users. I personally have been supplying solutions for professional photographers for more than 15 years their needs are special mainly file sizes, storage and performance. I would hesitate recommending the iPad as the be all end all answer as it is not. It is not the right product for the job. However as presentation device it is excellent. I agree that the upload and picture management needs to be addressed but again i suspect that will happen either with software upgrades from Apple of from a third part developer.
I do agree that iTunes needs an overhaul not that this was mentioned as it has become bloated by the huge number of content available. I suspect that will happen in early jan or first half of next year when they release the new store for the Mac OS platform