Honestly, I started out with like $20 to my name and ended up always making huge profits. And, when I say huge profits, I mean huge ROIs, not necessarily that sales happened often... There is a lot to learn in this business, but I think having some good business sense and knowing human behavior and psychology and having a firm grasp of the English language are basic starting points. It's mostly speculative. Either you are in sync with the desires of the universe or you buy crap that no one else wants. Some people know what quality is from day one, some constantly buy crap for years. But, in the end, if you want to make money you have to treat it like a business and always be selling...
I'm just getting back into domaining myself after a few years hiatus. In the past, I mostly picked up some names at registration fee and flipped for $xxx - low $x,xxx sales. Like I said, huge ROIs, but sales were far and few between. But, I wasn't always selling, I was mostly BSing and socializing.
Also, if you're living off this money or use it to pay bills or buy that shiny shiny instead of reinvesting it back into the business, you'll never get anywhere, trust me on that one. Get a job, do this on the side. Save, save, save, invest, invest, invest, that's the only way to financial freedom