I went straight to VCarve Pro myself. I messed around bit with CC but I don’t like it personally. Some folks have figured out how to milk a lot out of it. For me… I just need to get stuff done, quickly and efficiently and VCarve does just that after you get past the initial learning curve - no matter how complicated a layout you have. The community behind it is awesome and it’s pretty much the standard for small CNC shops so the choice for me was clear.
As Will mentioned, Vectric really has about the best upgrade policy in the software industry. If you ever choose to upgrade to a higher package, all you pay is the balance above your initial purchase… nobody does that that I know of. Their demo/trial policy is also among the best in the industry… so create your first projects on CC and start learning VCarve for free.
To be honest… my choice to go straight into VCarve pro actually set me back in the shop by about 2 months. That is because most of my projects are fairly complicated though and I had never used a pro level program for CNC work… there was a lot to learn as I forced myself to jump into the deep end of the pool… but after that initial period of learning and experimenting was over… it was like that first ride on your bicycle when you removed your training wheels as a kid… nothing can stop you now 