I was in a similar position to you and made it work out and actually paid for a family plane in the process. I was 30 when I started flying, knowing I wanted a new second career after leaving the enlisted army world. Although I went to ATP because I wanted a set schedule and open access to training aircraft (the local FBO only had one trainer), I would do it a little different if repeated. I bought a C206 right after getting my CSEL (a C182 would be much cheaper and still work) so I could hire myself to do part 91 parachute work. If I were to do it over, would buy the airplane from the start after finishing my PSEL so my insurance rates would be lower and I would be building time in my own airplane. If you have the cash to buy a plane, it is really cheaper to own for time building as opposed to lease. A Cessna will resale for the same you bought it for with only a slight drop value do to engine reserve. If you go on dropzone.com or similar websites, almost every region is looking for weekend jump planes and pilots. I leased myself out with the plane to do DZ parachute work on the weekends, and got my cross country time ferrying the aircraft to different DZs. I will admit, it was a lot of seven days a week work, I worked my regular job then flew for hire on the weekends, but I was able to get ATP mins in under two years and paid for the plane and my flight training. It is easy to get 10 hours a day tach time flying at a DZ, and DZ's pay for the ferry time as well. 25 hours over a weekend at $200/hr/dry (maintenance reserve is $45/hr on a C182/C206) gave me $155 to put towards paying for flight training and the plane. Insurance and overhead cost me about $80/hr. I actually grew to the point where I bought a second plane and hired another pilot to fly it. At the end of my project, I sold the C182, kept the C206 (which was almost paid for) and had my student loans repaid. I didn't want to fly piston jump planes my entire aviation career, but it got me into the aviation community and I didn't pay for any time building. I had no issues getting good paying jobs in the DOD contract market, if you're into that kind of work, and I was able to move into the DHC-6 and B90 with sub-750 hours because I had a relationship with a DZ owner. That relationship that was made while flying for him in my own plane. Six years later and I'm making captain's pay in an overseas job and loving it, with no aviation degree and no loans. My advice- buy an airplane that someone will pay you to fly. Get a CFI rating and a 18K C152, teach on the weekends and do photo flying. Get the higher performance plane and do jump work. There are plenty of great ways to pay for training and time that don't require regionals, or any 121 work ever. No union, no seniority to worry about, and you get to fly all you want. Oh, and you get to learn how much easier it is to fly for someone else than try to have your own company!