The work flow on most CNCs is very similar. You need to create/find your artwork, create tool paths based on the artwork, post process into a g-code file, learn to open the file in your sender/controller, zero the machine on your stock (corresponding to the zero point in your design file) and then start carving. Any machine will require the exact same steps. There is some difference in the different software you use to create toolpaths and operate the machine, but the overall process is the same for every machine. Nothing is just Find a file, click a button and go. There is a learning curve (it is quite a bit more involved than a laser or 3D printer). No shortcuts, but certainly no insurmountable hurdles either. Having a rigid, reliable machine makes things much easier, because you are not fighting mechanical issues. Determine your requirements (size, materials you want to cut, special feature like being able to clamp stock vertically for joinery cuts, etc.) and then buy the best machine (NOT cheapest) you can afford that meets your requirements. If possible, stay away from GRBL controllers, machines with belts or plastic structure. Rigid and fast is good. A $1500 budget will not quite get you past the GRBL based, belt drive machines, unless perhaps you are willing to go quite small (12’ x 24” or so). There is cad/cam software available for Mac, but although I do all my design work on my MacBook Pro, I do use Bootcamp to run some windows based software.