Mark,
As a self-taught ShopBot user, here are a few ideas I can offer:
Right now the most popular (and recommended) software is coming from a small British company called Vectric. They offer an entry level package called Cut2D, a more complete package called VCarve Pro, a 3D package called Cut3D and a photo and imaging package called PhotoVCarve. If you go to their website (link below) you will find a good collection of videos and tutorials for their software. If you download the demo versions, and spend some time with videos and tutorials, I think you will see how easy it is to design and program the machines. The demo programs are full versions (but will not allow you to cut anything but the demo designs) and all have a very impressive simulation output which will show you on your computer what the finished project will look like. Their programs also support all the affordable entry level machines as well as homebuilts.
Vectric's website is at
www.vectric.com and you will find the training materials under the Support tab. Their forum is also top notch and you will find a lot of new users their asking for and receiving help and guidance.
If your interested, there are a sampling of projects in my gallery all made from the Vectric programs.
Another valuable resource close to you is ShopBot in Durham. They currently make a machine that might be in your price range called the Buddy. Also, they offer a series of training classes starting with a 2 day course for $300. If you purchase a ShopBot you get some of the Vectric programs with it and the training covers the software.
If you are getting into CNC as a hobbyist, I would recommend the self-taught approach. You have time on your side. If you are looking into it as more of a commercial venture, you need to start making money pretty quick and the purchase of a machine like a ShopBot, with their training, is probably the best way to go.
ShopBot's website is
www.shopbottools.com
Like Vectric, ShopBot has an excellent forum where people bend over backwards to help the new guy. The response you will see from either forum is similar to the support you can find here.
Bottom line is this - if you already understand the concept of routing wood, feel comfortable with a computer, and are willing to spend some time viewing videos and working through tutorials, you can be making projects within days.
I hope this helped.
Tim