I do everything design wise that I need through Illustrator. My roland came with CutStudio which they have a plugin for Illustrator, so when I get ready to do the actual cutting, I use the plugin for that.
Now, I have heard of some people being able to do their cutting straight from the design program like Ai or Coral, but I'm not up on that too much. It might just be as simple as setting the printer setting to your cutter, I don't know. I'll need to investigate that.
As far as software for designing, I would go with something like Illustrator or Draw and they will be there when you have to do more intricate work later on.