You need to be good with numbers, but dont worry about it too much. Lots of help pages and solutions on screen on most modern CNC machines.
I run Haas Mini Mill, Daewoo Puma Lathe and next week CMZ TL lathe.
I self taught, as the guy who was running the CNC machines left quite suddenly, i was a manual guy mostly on Milling machines. I have been at my Company 20 years this month and still love it, now a machine shop Manager and on a good wack.
A bonus if your a proper car nut, is you will be looking for things to make.
Software, Solid works is cool as recognized all over. Cheaper options Alpha Edit, Bobcad, Edgecam and One CNC which is what i use for Milling.
I write long hand still for the Lathes, bit old fashioned and time consuming, but helps learn and take in exactly what your asking the machine to do.
On the newer machines for example CMZ Lathe, you can use it's system called 'Manual i' so the computer allready has set templates be it turning, drilling Threading Cycles, you just fill in the parameters required to make your part.
If you have no machining experiance, then it may be wise to get yourself to a local machine shop and even check out some manual machining, it will teach you workholding speeds and feeds,and how to plan your job.
Good luck, and most of all enjoy it.