PS, my "simple" life is actually kind of complicated. Got out of a typical mortgaged lifestyle, seriously cut back on everything, got rid of most stuff. Upon our split, my ex-no.2 ended up as she had been living, in a 1br apt, downtown area, no car, most services in walking distance. I'd take her to the grocery store shopping every week until summer, when she began riding her bike there.
I planned on moving into a van, which even now serves as my bedroom as I live with my mentally disabled son AMs and PMs to help caretake him... at his apt in ex-no.1's basement.
Part of my plan was to bank mad cash, working a professional publishing job while living cheap, with various PT jobs on weekends. So far, that's worked out.
Also, renewing relations with ex-no.1-in-laws has led to construction of a tiny house, aka a sugar shack, on ex-no.1's land with recycled bits from the farm and wood cut from deadfall off their own land. I told them my motives for building it and they are totally on board. I'll never own it, but I can live in it as long as I want or they let me. Part of the deal was resuming work on the farm as a PT meat cutter and taking on additional responsibilities on the beef slaughtering end of things.
But there's no way I'd have an opportunity like this if I hadn't previously put in nearly two decades with the ex and her family. They know and trust me. I'm useful on the farm. For the most part, I'm building the shack, something they just never got around to in something like 6 years. And in spite of a majority of free material, I'll still have a few hundred dollars into it, plus all the labor I'm trading.
Another PT job as bike mechanic resulted from working 5 years as a FT mechanic, a job I landed after a decades long customer relationship with the LBS. We also went to school in the same town, at nearly the same time, had mutual friends and acquaintances, and worked at different times at the local grocery store, with the same boss and co-workers.
Guy I know lived in a tent in the woods... in Maine... for a whole year, which included severe winter conditions and even the tail end of a hurricane. But again, he was gainfully employed and the land where he resided was a loaned plot... from a guy he knew and with whom he had a working relationship as the land-owner's weed dealer.
Living simply in a small structure, a tent, or even a van can be done, and even for not much money. But if you don't have money to make yourself useful to the people on whom you'll be leaning, you better have something they need or a personal relationship to make up the difference. Most of the time, those with access to give didn't get it for free and aren't hanging onto it for nothing, either. Pretty much everything cool I'm able to do right now is a result of decades of relationships and work along the way.