Sounds like you've never tried this freedom that you speak of. I've been doing the 3 things on your list for the better part of 10 years now, and I've never been wealthy.

3. Living on the road is no more expensive than living anywhere else. Less usually, since there's no rent or car payment involved. I can live large in Thailand for $500/month.

2. Living on the beach, I once calculated that I needed to bill one day per month to break even. Anything above that went into savings. That leaves 29 days a month to do whatever you like.

1. During those 29 days per month, I work for either a.) myself or b.) nobody. Maybe once a year I'll take a short contract, pull in 20k or whatever, and repeat for another year.

And that's just the level of effort needed for subsistence. Any money earned above that goes straight in to the "retirement" fund, in quotes because frankly I consider myself retired today.