Nice post Wildpilot,
I find myself in the same boat, and have told myself that I like it. Just coming up on 4000 hours of flying, mostly in Alaska. All single engine piston, floats and wheels, and VFR (sometimes very marginal VFR to be sure).
I am also 40, single (now) and basically broke. I have no health insurance, retirement plan, and my main employment is just as fragile as my next medical exam. I am lucky in that I am an A+P mechanic, and that has at times been a lifesaver when it comes to a paycheck.
I do love the flying though. Flying in Alaska is always challenging, the sights and weather are ever changing, and it's nice to be a part of an important supply line to people who need you, and generally appreciate you. Especially when you can do it without scaring them too much, at which I have (fingers crossed) been mostly successful.
The pay is not bad. One can make a decent career out of it if with the right company, but I am worried about my future. I am really out of the loop when it comes to instrument flying in "the system", have no turbine time, and very little multi engine time. That in itself makes it hard to contemplate the move to a company outside of Alaska, as I would be competing against pilots for whom those things are a piece of cake, for less money most likely.
I am not sure I would be very good at being a copilot.
All in all, I'm happy, and feel lucky to be able to do what I do. Although sometimes I have to remind myself of that.
Stay safe friend.