I don't think you'll find too much negativity about what you want to do...most of of us understand why you'd want to do it. An airline job for me is kind of a compromise, it provides (in theory) a flexible lifestyle, income and benefits, and the ability (via commuting) to keep roots for family and spouse's career...I also get to fly airplanes for a few minutes a day.

JohnBurke is right of course, what you need is tailwheel time for starters and float time. ME time is something you'll probably need too to maximize your opportunities (an employers insurance company may require that). If you get the opportunity to build turbine time (maybe in a 'van) do that too, it just widens your opportunities.

Airline and business pilots should have a college degree...for what you want to do an A&P license would be very, very helpful especially in Alaska.

Alaska is probably where you want to go to make your bones, all kinds of float and bush opportunities obviously. I think some of the Alaska pilots even do seasonal migrations between AK and the Caribbean.

Hang out at the airport, talk to people, hopefully get steered to some opportunities. I hear they are short of CFI's in AK, and that the CFI's generally move up to bush flying.

Where you're going, you'll eventually be tempted by an opportunity to transport unlicensed consumer chemicals...let me suggest that you pass on that.