Been thinking about pilots license and a twin turbo prop (8 seater). It's gotta be able to move the whole fam damily. That's about 350-450k. But I am not in that good of a position. I'm thinking the classic truck is the best idea if PT and PL seem to be a no-go.
As an ole IFR pilot, I strongly recommend you get your pilots license. There's so many good reasons why you should do this, it is hard to know where to start on the list.
I will start with something you might think frivolous: It is
FUN. I mean, deep-down to the soul fun. Your first solo will be remembered with the clarity of the first time you got laid. You'll never be as happy to lose a shirt-tail. Moreover, there is a very real subculture out there. You will meet folks with the ice already always broken. And the percentage of stackers/preppers is disproportionate to the general population. <-- TINS
Another reason: Even if you do not
own your own plane... think about it: You are out in the middle of nowhere, and there are cars all over the place, left there for use by absent drivers. And you really have to get somewhere fast. But you do not even know how to turn a car on, much less drive one (at night, yet).
So lets look at that useless conglomeration of cars you cannot use, and turn them into small planes...
You could rent one, or fill in for someone who owns one but is incapacitated and cannot pilot it. Or buy one. Or steal one.
A circumstance where even a dinky little Spam Can can be better than any vehicle: Roadblocks. A Piper Warrior carries four. You do NOT need an 8-seater twin-engine plane: You can safely fly your family up, over, and past any block at all by just making more than a single trip. Mileage cost/difficulty in fuel, maintenance, etc., for a twin turbo-prop 8-passenger is an order of magnitude greater than the "chocolate bar wing" single-engine. <-- Which can take off and land in a third the distance.
To encourage you: *IF* you blow about three or four Krugerrands worth of fiat to earn your IFR -- you will discover a crazy fact: If you can fly a single-engine, fixed landing gear, static-prop dinky little plane, you will be shocked -- if you ever get the chance -- to discover you can fly essentially ANY plane.
Compare it to getting your driver's license: Sure, you could drive any make of car... but... oops! You could also now figure out how to get that 18-wheeler going, couldn't you. Or a bus. Or a tractor. <-- Those are only different kinds of "planes", d'ysee.
Dunno what else I could tout to get you to go do it. It sure as hell fits a prep requirement.
WAIT!! LATE EDIT ADD: Here I yam, 82 (jeez!) and I find there were times when each of these three things reached at least temporary parity: Sex, Scuba, Flying. <-- Now... you doan wanna lose out on a Trifecta like that, wouldja? 'Cause you most ricky-tick will if you don't indulge in all three. Like we useta say:
There It is.