I would say, enroll in college w/ a flying program and have the post 9/11 GI Bill pay for your degree and all ratings. Aviation degrees are not usually the best choice but that's what it takes to get the GI bill to pay for both. You'll be able to check the square and today my friend that's all that matters is checking the square. you'll have a degree and a CFII/MEI in 4 years and have 4 years to observe the market and think about what you'll do next. Also if you could narrow down your geographic constraints that would help people help you.