Welcome to the forum John, I actually started out with Cut2D because as a signmaker I already had expensive software to create my designs & was only looking for cam software to toolpath for cutting.
Soon realised that Cut2D wasn't going to do all that I wanted so upgraded to VCarve Pro, price as Adrian has said was just the difference in price between the 2 programs
I now run Aspire & the upgrade path is just the same, you only pay the difference between the two programs, so it really doesn't matter which of the Vectric programs you start out with
If you are unsure if you should start with Vcarve & upgrade to Aspire at a latter date or just purchase Aspire from the start then your best bet would be to download the trial software for Aspire as you have done with Vcarve & have a look for yourself. The major difference between the two programs is that Vcarve can't produce 3D models so apart from the modelling tab the two programs look the same
You could start with Aspire but leave the modelling until you have a better working knowledge of the software although I must admit for me the temptation would be to great for me & I wouldn't leave it alone lol
As you already have experience with Cad/Cam software & running a CNC machine you shouldn't have any problems with Vcarve, lots of tutorials that are easy to understand & if that isn't enough there is the forum