I'm so sorry. I've always recommended Specialty because they've always been responsive to me.
If you'd like to call Graphtec, their number is: 800-854-8385
I would hope they'd support their CR, but if they say they don't, don't let them off the line without giving you a phone number of the CR tech support.
I really wish I had one of these machines to test so I could either confirm that it's junk or be able to give people suggestions. But by the sounds of it the process is a little different from the larger CR Pro and CE5000-60.
I'll be trying to help someone else to get theirs to cut, period (he's having connection issues), but I honestly don't know how much I'll be able to help because of the differences in these machines.
If only I could get Specialty to ship one of these to me to test, but I'm pretty sure that won't happen, and I just don't have the money to spend on a plotter that I'd never use on a regular basis, even if it is only $300.
I can certainly understand yours (and others') frustration. Things should just work, and it's horrible when they don't, especially when you have such high hopes for them.
I apologize for telling you that this plotter might work for you.

I ordinarily don't suggest this machine, but the CR Pro instead.

I can see that if it's this much trouble just to get a simple contour cut it's just not worth it.

I wouldn't blame you at all if you returned this plotter after the trouble you've had!
If you'd like me to try to contact Specialty for tips, I can certainly try.