Is this a good idea?
I am a 32 year high school teacher with a PPL (80TT) from when I was 17-18. I spent several years in the Army as an infantry officer and am currently in the National Guard. I would like to complete my IFR, commercial, multi, CFI and build to 1500TT so I can fly big time. Honestly, I would like to fly 121 but I'm open to 135 as well. Or fractional (a coworker's husband flies for Flex and it sounds awesome). I have a bachelor's degree in criminal justice and a master's in educational leadership.
I have a wife and two young children and we own our house in DFW so relocation isn't a great option, but commuting and being away from home isn't anything new with my military background. I figure I can do all of the training on the side until I'm at 250TT, and then fly CFI full time until I can obtain an ATP. I have some GI Bill benefits left so the training cost isn't too prohibitive. I currently make around 57K and I can't drop to minimum wage, but I can afford (between savings and NG) to make a bit less than that while building my hours. I could also keep my day job and CFI on the side if that's what it takes (I'll have to measure the trade off in terms of longer overall time that will take).
I don't have the best history, but I'm capable of being perfectly honest about all of it:
-I have a number of speeding tickets. Two in 2004 (I was 17), one in 2012, one in 2013, one in 2016, one in 2018. I also received a citation for running a stop sign in 2018. I paid all of these in full and I checked my record- I think the 2016 one isn't on my NDR because I took a defensive driving class (I will still disclose it). I know I need to stop this immediately.
-I received a summary (essentially, a traffic violation for a non-traffic offense) citation in Pennsylvania for disorderly conduct in 2009 (age 21). I paid it off the next day.
-In 2011 (age 23), I hit some rough spots in my military career and voluntarily checked in to the base hospital for mental health. I stayed there inpatient for a week and did a few months of outpatient therapy. I took some meds but nothing that lasted beyond August or so of 2011. I have taken nothing since and have had no issues since that time.
-In 2005 (age 17 or 18), I failed my PPL checkride. I came back two days later and passed.
Honestly, I'm going to do this one way or the other. I need a hobby. I just want to know what to expect. Should I be content with doing CFI on the side for the rest of my life, or would 135/fractionals consider me, or would I have a shot at getting in at a major (if I avoid busted checkrides and speeding tickets for a few years)? Let me know, and thanks in advance!