>Acquire the free time and money to not have to work,

I do a lot of work while walking and hiking; as a programmer, most my time is spent thinking which I do not need a computer for. Well, I need a phone or tablet to find stuff on internet to think up a solution, but I can do that during walking. And I do. It won't give me a month of 8 hours / day, but it does give hours of walking per day. I did hikes of 4-6 hours / day in fulltime work days while sleeping / working in hotels on way points of the hike. 4-5 hours of walking/dictating/looking up stuff and then 2 hours of typing in/testing/delegating when arriving at a hotel.

That's really interesting did you document any more about your process?

I was going to do that but did not yet. I must say that I generally try to do not do any 'frontend' stuff. So sure I do prototypes of the frontends but someone else does a UX/UI and the coding of that. So my thinking is architectural, the different components, algorithms and low level implementations. All of these I can work out in my head with some Google + paper which means I can walk during that. If I would have to do HTML/CSS it would not work; I am not sure if that's because i'm just not that fast with it, but it's way too much iteration to not make me sit in front of a (large) screen for too long. For instance, when I have to do embedded work, thinking up the coding, let's say for a RISC chip, can be worked out to quite a lot of detail before typing 1 line. Worse; if I don't work it out in detail, I'll just end up frustrated behind a debugger and a lot of crashes. I have done that since I was young as assembly or low level C never worked well for me while iterating; only in recent years I realised that this applies to other projects as well.

Another thing that has to be said is that peripheral vision is important; when I walk writing or staring in my phone, I don't have issues tripping, walking into things etc. I would be very handicapped if I did not have that. And another thing with my eyes is that I read very very small print which is why I can work quite comfortably on small tablets / computers (I am looking forward to receiving the Pyra).

There are plenty of people hiking the AT who are decidedly not wealthy. Heck, I've met quite a few hikers who hike specifically to save money (living off social security).

I found lots of folks on the AT who weren't Silicon Valley wealthy (although I'd say more of them were than I expected).

But almost no one was actually poor, as in, had ever lived hand to mouth, or couldn't call in family support at a moment's notice.

So I'd say everyone I met was much more wealthy than anyone who's really poor in the US.

Certainly there are exceptions, but the general assessment that thru-hikes aren't for the poor seems sound to me.

No, that's irrelevant because of all parent's 3 points could easily be part of a job like land or mineral surveying, field biology, forestry, and so on. You don't have to quit working to go outside and walk around all day.

I always wanted to be ....

A lumberjack!

This isn't realistic for most people. How many foresters/ mineral surveyors are there?

Not realistic for many people who live far from rural areas.

Or have an outside office with stand up desk and treadmill.

Run, walk or cycle to - or part of the way to - work. Problems solved