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BrokenAbyss Exactly. I was reading all this and wondering where to jump into the conversation. There's ways around the "system" and some people are a lot better at finding them than others. A guy I once worked for owns property in two states and at one point owned a large boat in a third. Up until a couple of years ago he had a house here he was using for free during the winter. I'm not sure where he is or what he's doing right now, but before covid he traveled, not just the US but the world, and he did all this without having a "job".
If he wants to go skiing he knows someone who works at a resort. They'll hook him up with free ski lift tickets, a place to stay, and loan him their spare vehicle.
A trip to Germany? Old army buddy living there.
Philippines? He meets a woman on a ferry and by the time he gets where he's going she's offering him a place to stay.
Hawaii? He went a few years ago and by the time he left he had new friends who were willing to let him sleep on their couch, on their porch, or pitch a tent in their yard. Oh, and another friend worked for an airline and the flight only cost $100.
He's always looking for a deal and there's always someone willing to help him out. I won't say where, but he owns a cabin in one state that was built with lumber from the opposite corner of the US. It worked like this, a business owner had a bunch of scrappy lumber in a warehouse he needed cleaned out so he offered it dirt cheap to my friend, but he managed to negotiate an even better deal. Then he calls up a truck driver he's friends with and arranged shipping, no doubt at a really good price.
If he needs money someone will hire him, sometimes for a job he isn't qualified for. They most likely will pay him as much as or more than the going rate and put up with him taking a vacation right in the middle of the job. If he gets in over his head there's probably a number programmed into his phone for someone who knows something. I've gotten these calls, "Hey, have you ever......I've got a problem..." He once did some electrical work while traveling through Europe. I wouldn't have hired him to put a plug on a cord but he managed to pull it off.
People always look out for him and look the other way when he needs them to. Propane bottle 10 years out of date? No problem. Not only can he get it filled but the guy filling it will be so glad to get the it back out the gate he doesn't charge for the gas either.
Personally I don't live the kind of charmed life he apparently does, but at the same time I tend to play by my own rules and don't feel obligated to do things a certain way just because everyone else does. It's possible to live cheap as long as you can figure out how to get free from the system.
