I agree with pretty much everything mentioned so far.
However - am I the only one who has a hell of a time getting CutContour lines to work straight out of CorelDraw? I used to have no problem out of X3 but with X6 - anything with a raster image in an eps or pdf I've had to launder through Illustrator and flatten for Versaworks to pick up the lines.
A "hot folder" option would be nice - I use it a lot with SoftRip - where it will pre-rip files you put in the folder, based on the default settings.
The ability to add a certain spacing between the prints every X feet would be nice. We do this manually every 15-20 feet of printing (large run stuff) for the guys who run the laminators, just in case we run into problems and we have to slice the job. Not sure how you would implement this, though.
Option to auto-save jobs after they've been ripped? So many times I'll manually nest a job I printed but haven't cut yet, only to find some knucklehead decided to clean out the queue list before I had a chance to cut it.
An estimated "time left" option for a job that's currently printing would be VERY helpful! Currently I can only see how long a job will take to print by going to the Print Quality Settings, but you can't get into that when a file is printing.
+1 to 2B's suggestion to pick multiple files. I know I can drag and drop, but it's annoying you can't just ctrl+click multiple files from within Versaworks.
I'd like to also chime in with Splizaat's comment about borders (and selection of color) - I would LOVE to have this. I often create files where I need to nest them together - but if I'm printing four 12" tall files to go on to a sheet of dibond where I have no wiggle room that I will shear after the fact, adding the trim lines that Versaworks has creates too big of a space for this to be possible. A hairline that gets printed to the inset edge of the graphic would be a time saver.
Nate really makes me want to try Caldera...hmmmmm.