My idea would be for a crap weather place with bad winters. Basically you'd find some place in the forest with a reasonably short and good path, but for whatever reason is nearly impossible to find for people, maybe it's inaccessible without your rope and metal ladder, or what have you. It has good drainage, an empty space in the middle that is surrounded by trees. You walk out of there and you are practically in the city, on some trail that leads to the gym (showers, working out), grocery stores, and a place of employment.
Now the difficult part here would be the requirement for some sort of platform off the ground and there is no way around this other than building a patio style platform. You need a solid place to build off of, you need to stay off the ground to insulate you from the cold, etc. This is where a lot of your building budget would be spent.
The rest of it would be very experimental. I'd want to try and find a way to make a warm insulated room for as cheap as possible. It's basically just for sleeping and browsing your phone, the rest of the time you spend working.
Like, could you make roof tiles from these?
Could you make a basic frame for the room with 550 ft/p strength paracord?
Could you wrap it in so many garbage bags, duck tape and bubble foam that it would eventually be as warm as a house? If its not warm enough you just keep on wrapping more and more layers. Eventually it would have to get warm with all the air pockets.
Roof would be tricky because you need something hefty that doesn't blow off. a ton of paracord and a tarp might suffice.
Could insects burrow through the plastic? If so you could do a layer of aluminum foil.
The idea is that you set up a hammock inside of it, and you have a ton of warm wool blankets, and you are completely warm in the worse blizzard, and in the summer its tolerable and insects aren't getting in there, at all.
Anyways thats always been fascinating to me, the idea of using all these cheap sorts of materials to try and zerg your way into a living situation. Its so cheap that if you actually figure out something that works well, you can expand cheaply, and you could just have a spider nest style house spreading across the forest floor.
Of course maybe I'm complicating crap, there is this guy: