I built a business that lets me live on the beach full time
expatsoftware.com
expatsoftware.com
I contracted for a year 7 years ago from Asia and I was able to travel the world during this time. It was definitely a great experience.
Now, I have been remote contracting for almost a decade and it's given me the ability to build one successful business and I'm now in the process of starting another.
Distractions and commute time really destroyed my ability to build a side-business...and working from an office was exhausting.
If you want to start a side-business, but aren't ready to take the risk (or just don't have the money), start by contracting remotely.
These folks would disagree with you: https://www.bumfuzzle.com/us/
Yes, you can't have a mortgage, and you do need to find a remote income source (in their case, based on the information available, it's options trading to scalp enough for monthly expenses). But it can be done if you're willing to trade some financial security for freedom.
Addendum: List of blogs of families living full time on a sail boat: https://www.sailingtotem.com/blogging-families-afloat
Financial security IS freedom. If you have enough money, you can do pretty much whatever you want with your life.
"it's options trading to scalp enough for monthly expenses"
If you have anyone else to support besides yourself, and you are only making enough for monthly expenses intentionally, so you can enjoy your life in an exotic location, you are doing a complete disservice to those people.
One bad month or emergency, and they will suffer...and options trading? You might as well be gambling at a casino.
I know it can be done because I know more people than I can count on my fingers who have done it.