I've been thinking about getting into milling (wood, or freaky candles) for a while now, but I can't tell if my lack of familiarity with CAD software is going to mean I stink at it forever. How hard was it to get into? Do you have special training from a trade or anything, or did you just pick this up as a hobby?

No training except for googling stuff and pestering their customer service folks.

I learned openscad from the tutorials. I use meshcam to generate tool paths. Mostly I use python to generate the source art and just cut that out.