For your image-problems Drupal is a good solution cause it can handle the image processing awesome. I had clients drag & drop a 25MB cmyk jpg into the wysiwyg and wondering why the page is slow. Solved it with just 1 additional module. Also Drupal handles the processing really well, especially when you define different fields no client can do anything wrong and whatever the client uploads (portrait pictures for defined landscape ones …) it can create the version including intelligent cropping with e.g. face detection to produce teaser images of various formats in exactly the dimension I defined and also optimized to the device and bandwith.