I'm the onlyone running it... well, 2 others know how, but they barely run it, and they do it the same way as I do so theyre used to it.
Sometimes we cut 29.9" out of a 30".... so poll sizing doesn't work. Poll sizing you tend to lose half an inch or so!
Honestly, the only downsize is the crosscut function is dangerous to use because it can cause jams. We never use it anyways... I just pop the lever open, push down on the crosscut blade and slide it myself.
but generally you have 24, 30, 48, 54 and 60" Material... I just set whatever size roll I'm loading into cutting master as the size and it'll never cut past that. I really only do a "roll setup" once a month, or sooner if I have a media jam error. It's great... you should try it for a week! It's especially awesome on 54" Print and cuts that have the marks right to the edge... I can throw a 54" anywhere on my 60" plotter and it'll read and cut them fine.
That being said we have 5 arms on our cutter...so I tend to keep one on the max outside and just use the other 4 for the inside. So even when I re-poll I never really have to change anything.