Well, with an opportunity to go commute to the local college and use their flight school looking less and less likely ($50k for all of flight school is too much for the parents), I'm looking instead to going to college for something else. My other love is computers, so I'm thinking of going into IT.

Yeah, IT wouldn't be bad at all and I'd enjoy the heck out of it, but it ain't flying. So what I was thinking is that I could get my flight training done on my own on my free nights and weekends throughout the year. Then, somewhere down the line, I could move less into IT and more into aviation. I was thinking that when I got my CFI/CFII/MEI, I could move into CFIing full time and working in freelance IT/web design to help pay the bills and build time. If I never got latched on with a regional, I could just go back to IT and fly on my free time.

Anyone ever go down a similar path, where they worked and trained on the side and have their story to tell? Am I just dreaming right now? And if I were to go down this hypothetical route, how long would it take to get all of my ratings?