EDIT.....I just realized you actually have a different issue. I just tried doing what you want to do and I do have the print/cut setup available both before and after importing and image. For reference I can tell you that the "print" on the top menu bar is greyed out in my Cut Studio until I select the print/cut option in the drop down under file. I do not know why it is unavailable on yours.
There is a workaround, it's a but cumbersome but it works. We have a veracamm now so I haven't used this method in a few years but I found instructions I wrote for someone else who was having the same problem. I've posted the steps below. If you have any questions on the process let me know.
I haven't had the time to write a "how to" so here's a basic outline of how we do it. If you have questions on any particular step let me know. I realize you are using different software for design but the basics are the same. Also, this isn't necessarily the only or best way to do this...it's what works for us using what we have and without spending a lot of money to streamline the process.
1. Design graphic for printing as you normally would, making sure to create a vector cut contour around the image. Before printing add 3 registration marks (black 1mm solid circles), in the lower left and right corners and the upper left corner.
2. Print design with reg. marks.
3. Delete everything EXCEPT the desired cut line and the reg. marks.
4. Export as an .eps
5. Open Roland Cutstudio and import the .eps file.
6. Click "file", "print & cut", "file", "printing setup"
7. Click the "setup printer" icon and put in the size of the piece of vinyl you will be cutting.
7. Adjust the crop mark location in "printing setup" so that it matches where you located the crop marks. Note that there are some limitations as to how far apart you can put the marks so it's best to test your locations before you actually print the design.
8. When you click "okay" and return to the main Cutstudio page you should see 3 grey circles which represent the crop marks. These should line up with the blue cut lines, from the .eps, for the reg. marks. Note...it's not necessary to cut the circles. You can delete the cut lines for them if you choose but we usually don't bother.
9. Now you can load the vinyl in the plotter, oriented as it is in Cutstudio. Once you have it loaded move the optical sensor area of the head so that it is in line with and slightly to the left of the lower left registration mark. Do Not set the origin!
10. In Cutstudio select "Cutting" (top menu bar) and then "OK"
11. Plotter will find the lower left, lower right, and then the upper left registration marks. Once it has found all 3 marks it will begin cutting.
That's the procedure! If you have questions fire away. Good luck.
Bill