But it should take it up with continuous cutting on, that's the point - in onyx I will print barcodes every 10 ft..... With the segments 2 ft apart. It'll read the first barcode... Cut the first 2 ft, roll it up, cut the next 2 ft... Roll it up, etc - it'll get to the next barcode... Continue cutting, and continue rolling up every 2 ft. It's how both onyx and cutting master 4 / cutting master 5 perform.
So if it doesn't do it in caldera.... There's either a setting, or caldera didn't design it to do it that way - I would reach out to them and ask them if there's a way to enable it or not, it could be a setting hidden deep in a menu you'd never think to look at.
And I agree - we pay good money for our rip softwares, if I had to use a free illustrator plugin to make the. Utter work the way is want, id be annoyed - if I couldn't do roll to roll cutting with take-up on it, I think I'd swap to a different rip.