Jeff,
Some machines have better user "front ends" Biesse and Weeke come to mind.
Some machines require 3rd party software.
There isn't a person out there that can tell a machine what to do that isn't something you already know how to do.
If you want to drill a hole in a board you mark a location by choosing some distance from each edge to the center.
The machine software wants you to tell it that location using x,y,z coordinates, you figured out x and y with your tape and depth (z) you know if you are going through or not.
Same thing with a route or a saw kerf.
Start here, end there go this deep.
If you had a kid that could program that didn't know wood you would have to show him how to figure all those points.
I think you just need a little help on learning how to layout onscreen using a different "language"
Or you can choose to buy a machine, have someone train to run it and just learn how to turn it on a run a program as a backup operator.
When you get to doing irregular shapes from a cad file or photo then you need a better front end or someone who knows cad.
You could also buy Cadcode, use excel to create your geometry for standard parts and export to the machine.
Then when you buy a new machine that is a different brand spend 3-8 hours setting up the tool file to run that machine and use everything you already know.
Either way you can do it, its a small bump.
Feed speeds, tool rotations, cutter depth,joint tolerances, you know all of this.
A-