I personally took the manual route to start with when I started developing some different mechanical parts to a product I already made. I started out making the initial product completely by hand using routers, jigs, fixtures etc. Drill press or two, tablesaw and then finally came a manual X2 mill and lathe.
I then built my first cnc, which is a router.
I had planned on the next one being a plasma, but built a mill sooner and didn't need a plasma cutter then.
Third was a cnc converted lathe. Then built another from scratch. Now I have bought a larger mill to convert and that is getting parts shipped for it little by little.
You don't have to jump into anything full tilt.
I let my business do the buying and at first only worked at night building these machines. They were built for a purpose and are perfectly suited to what they do. Very little risk involved this way and my machines grew as the business did. I now have another full time employee and may be looking for a second soon. No reason to expand too fast I don't think. Just been keeping the books in the black and plugging away.
There is a fair bit of software learning curve that one must overcome, but it isn't as hard as say calculus.
Best place to learn that if you have questions is right here, so you are starting off in the right place and where I first knew that cnc machines where going to be a part of my business plan.
Good luck with it. tell us more about the project when you can.