Interesting thread. The theme of floatplanes keeps arising.....
Back in 2005 I did my ASES training at Browns - probably one of the tiny minority who actually get to use the rating - have a 1946 J3.
Anyway, there were 4 of us on the course - as a humble PPL I challenge anyone to find another place where you can learn, as comparative equals, alongside a Space-Shuttle pilot, a South-West Airlines Captain and a North Sea oil rig helicopter F/O. What struck me most was that all 3 of these professionals to a man stated that they did the seaplane course solely to get back to the basics of airmanship, stick 'n' rudder, no-computers, simple joy of flying. Really makes you think.
So, can you combine the simple life with the pay and benefits of a senior post in a main line operation? Almost certainly not. Not unless you own the operation. What you have to decide is how much $ is enough personally (you'd often be surprised how little you actually need, compared to what you think you need) then take the step. If you don't think you can do it, then you can't.
As they say 'life is short and when standing before St Peter, no-one regrets not putting in more time at the office'.