Sean, how are you doing. What part of mass are you from? What airport are you based out of? I grew up and learned to fly at LWM. I worked on the line crew for 4 years and used the money to take flying lessons. Am am in my senior year at ERAU in daytona beach and I can tell you, pilot and instructors down here are a dime a dozen. It seems like everybody is an instructor and they only have 1 or 2 students at most. If I had to do it over I would stay in a place where the competition is less and take on a steady flow of students. Be creative, the good paying jobs are still out there if you are willing to do your homework. Some of the best flying jobs are ones that are not advertised. There are lots of 91 and 135 flight departments around that would be willing to help an honest young guy out getting started by giving him a little duel in a king air or navajo or something. Just look up chief pilots names and start emailing them, you have nothing to lose. Thats what I did and it worked well. As for your rating and such, I took the 61 route and I loved it. Sometimes taking a little but more time to get your ratings will make you a much better pilot than being in a constant rush to get your ticket. Alot of incidental learning takes places when you work at an airport around airplanes. Consider working for an FBO while you are getting your rating. Its a free education in real world flights ops, unlike the sheltered 141 environment. Just my thoughts.....Joe