Brian, I began learning CNC machining in college. It was a basic introduction, but the experience made me want to buy a CNC mill. Nine years later I finally did. I sometimes work closely with the professional CNC programmers at my job and have learned from them, but I am mostly self-taught. There is always more to learn, and I learn as I go. I believe it is something within anyone's grasp who has a genuine desire to take it on, so dive right in!
People with solid experience in manual machining who know the "feel" of cutting metal have a great head start when it comes to CNC. Without that, there is much more fiddling around and missing what would otherwise be obvious.
Another observation is that small CNC machines present their own unique challenges, which require you to be more thoughtful, clever, and deliberate. The guy making chips on a Haas, Brother, Robodrill, etc. would probably stand to benefit from experience on a Taig or Sherline. Some pros may scoff at that, but whenever you have limited resources to work with, you become better at utilizing them and your work is more efficient. That is a fundamental truth which is widely applicable. Model engineers understand it well!
A third observation in going from small manual to CNC machining is that the consistency and complex control CNC affords improves your machine's effective capability in a way that is not widely appreciated. With CNC, more of a small machine's limited power can be made to go into cutting metal rather than the frictional losses associated with trying to do so. Learn about the concept of "chip thinning" and the calculations that go into feeds, speeds, and power utilization with low radial cutter engagement. Only CNC operation can allow you to take full advantage of this. I have done trials pushing my mill to its limits and probably set the record for material removal rate on a Taig, with calculated power exceeding the 1/4 HP continuous duty rating of the motor. Going from locking up the spindle and having to retram the mill doing pathetic cuts the wrong/inefficient way to ripping through with complete confidence is sure to bring a devious smile to your face!
Along the way, you will be making improvements and custom accessories to enhance your CNC mill. That’s all part of the fun of it.