One of the main issues, that costumers think is confusing and not userfriendly, is the way the system handles files, and especially images.
They often say, why can´t it be as easy as uploading an image to Facebook.
It would be really nice, if it was possible to drag and drop images and files to content areas when editing the website. It would also be nice, if it was possible to set the system to a mode, where the users actually dont have to go into to filemanager. In other words, if you wanted to add a file or an image, you should just drag and drop it to the content area. The system should take care of the rest.
The way umbraco handles Images is another way, that would definetely be a huge improvement. https://www.youtube.com/watch?v=tF03jgCgV7s
Can´t wait for the new UI, and hope the file and media managing area will be optimized.