It's Al here at a high school in eastern Ontario Canada.  A newbie to CNC with a recently refurb'd 36" gantry router, two Sherline mills and a lathe running 
Mach III.  As a sideline, I manufacturer a line of consumer electronic products using onshore talent and offshore production.  Gadgets for family fun. 
I am hoping to get a grasp of the basics of MachIII, LazyCAM and some student-friendly modelling program (tbd) so my students will be able to do a few  simple projects that they can be proud of.   However . . . 
As an analog guy from the old days, I fear the vagaries of software control and operating systems (and their endless updates) might make this impossible. 
With help from the friendly folks here I am hoping the learning curve will flatten quickly and chips will fly soon.
All good things,
Al