I fly, have had my license for a decade and change at this point. And recognize that AK is... weird. Flying-wise, the stuff that seems insanely high risk out here is apparently called "Thursday" up there. So be careful.
It's not a popular point of discussion on this forum, as it's something fairly few people here do (there've been the scattered "pilot" threads over the years with a few pilots posting, and a lot of people insisting that it's a stupid way to spend money). And it's not that cheap. Certainly more expensive than a bicycle habit.
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That said: Go look for flying clubs near you. Seriously, go look for flying clubs. Ownership is just about the most expensive way to fly, even factoring in some obscene rental rates, and shared ownership makes things far, far nicer. I'm part of a club out here, and dues are $60/mo fixed, a 172/160hp is around $75/hr wet, a 180hp 172 with a cruise prop is about $90/hr, and 182s are about $130/hr. Wet. That's Hobbs time, not tach time, so adjust as needed.
Flying is fun, I quite enjoy it. To get to a point where you can (legally) make money at it, you'll need a commercial cert, which requires a couple hundred hours total time - it's not something you can do with a private license.
Get your license and rent a bunch before you buy - unless you're buying something like a 152 or 172 that you plan to sell after a bit. They hold value decently, in proportion to engine hours left, as long as you take care of them. If you want some bit of equipment in the panel, buy a plane that has it, because it's far cheaper to buy it already installed than to have it installed. Drop $10k on panel upgrades, the value of the plane might jump up $3k.
In terms of ownership and costs, the big thing to consider is the annual cost. The more complex the airplane, the higher the base cost for the annual - and the more the parts to fix what's wrong, because there's always something or other acting up.
IMO, for most use cases, retractable gear isn't worth the cost. You can come awfully close to a retract with good wheel pants and fairings, if you're flying from paved strip to paved strip. And if you're going back country, which I assume is most airports in AK, "down and welded" is an awful lot stronger. Plus, insurance is cheaper - it's pretty hard to manage a gear up landing.
A constant speed prop, though, is an awfully useful bit of equipment - it might make sense. Again, it depends on what you're doing. If you're bopping from gravel strip to gravel strip, I might not bother, but if you want to get out of a gravel strip, and then get up and go somewhere, they're quite nice.
Go take a discovery flight, see if you actually like flying, get your license, and then worry about a plane, though. Unless you're planning to buy a plane to get your license, at which point either get a 152 if you and your instructor can fit, or a 172 if you're not a twig.