I'd like to have WYSIWYG. In the end, we see everything from the keypad side of the machine.
If designing a project in portrait orientation, I'd like to design it in that orientation, which is the way I'd see it as a finished project, then have a button to click that keeps everything in exact same relations while rotating and de-rotating 90 degrees to show how it will look from the keypad side of the CW machine. From there, save it to be carved. For that matter, even designing for landscape orientation, we should have a button to click to show how it will look from the keypad side of the CW machine, which is rotated 180 degrees from the way we see it as we design it.

Second, the processes between finishing design and starting to carve involves too much manual and mental labor. There is way too much confusion about virtual vs actual board sizes, use of sleds, keep under rollers, etc. I'd like to see the software enable sleds and carriers to be added onscreen, some software auto-help on what the sleds or carrier dimensions should look like, or user declaration of what sled or carrier size the user intends to use, and enough interaction between software and user that the project and carrier/sled can be just loaded and carved without much interaction at the keypad. In other words, answer onscreen (with assistance from software) whether to keep under rollers, where to center project, etc. Currently there are rules and scenarios that have to be worked out by memorizing rules or by experimentation, which the Pro software ought to be doing for us.