Others have covered most of the important parts, but I’ll add my 2 cents:
A bit of background: I had no CAD experience, but I was pretty good at Photoshop, and had a little Sketchup experience. I use VCarve and love it - it is very easy to use, and the video tutorials on their website are great. It has some limitations when it comes to complex parts that would benefit from Rest machining, (requires Aspire) but overall it is a fantastic piece of software and a good value. For a creative person, it’s an essential part of the CNC package. As good as CC and MeshCAM are, they aren’t the same as VCarve (for various reasons). With your creative inklings, I suggest that you plan to buy /some/ creative-oriented CNC software, like VCarve.
I tend to watch these forums and the Vectric forums for inspiration, but I usually re-design everything from scratch because that’s the part that I find really enjoyable, and it’s relatively easy. Remember that I had zero experience doing this before getting my S3. I realized that I love designing after I bought one.
The big question here is: how much time do you have to spend on your CNC hobby? Everything you are worried about is easy to learn, you’ll do fine, if you have time. Hobby CNC is exactly that, a hobby, and it takes time (and a bit of money) to do things right, but it’s so much fun you won’t notice either. It is a fantastic hobby, and I couldn’t be happier with my decision to get a S3.
Also, the Vectric trials only let you output gcode for their sample files… you can’t cut your own designs with the trials. (You can design things as much as you want, they just can’t be cut with the trial.) For that reason, it’s not really a waste to trial it before you have a machine. I think if you trial it now, it will be about 3 hours before your fears of design being hard are laid to rest.