I'm 47 years old, have spent ~30 years running a company that is slowing being replaced with changing technology, along with my entire skillset. I think it may have a few years left before it finally peters out. And without a college degree, I can't even get a call back in slightly-related fields. I've always enjoyed flying, but never considered doing it professionally until now.
I've been a pilot since age 22, collected ratings for the challenge of it, currently have an ATP AMEL, Commercial ASEL and ASES, and a CFI cert. I have done a few gigs as a CFI for transition training, but never had one primary student, and not sure how well I would do at it. I can't abide poor hobbs-watching CFI's who do a disservice to their students and aviation in general, so I'm not interested in doing that myself.
I have around 2800 hours (nearly all personal flying), of which 57 are multi PIC and 350 are SE TPIC, although it's my 2 seat, unpressurized homebuilt Legend, which probably isn't what most hiring managers would consider TPIC even though it does happen to have a turbine engine. I don't have an A&P cert, but I do enjoy working on my experimental and have built new avionics panels for myself and friends.
I'm wondering what's out there for someone "older, but not yet old" and with my limited experience. I'm more interested in enjoying myself at work than having a massive paycheck and no QOL. I built a little portfolio of rentals, so I have that income to supplement a paycheck. Not enough to live on, but will help close the gap with a starter job.
I have flown some trips in the right seat of a friend's company Hawker, and after the initial novelty wore off, it was a bit boring just tuning the radio while the AP flew for hours, so I'm not sure a jet job is the best fit.
I have friends who are heli pilots and they tell me about some of the coolest flying I've ever heard of... how realistic is it to go get my commercial rotor license, and how long before I could get any kind of heli job? I also enjoy the zen experience of quietly wrenching on airplanes in my hangar, so getting my A&P isn't out of the question either.
Are there any other airplane jobs out there that I could get and would keep me excited about going to work?