My thinking is to spend one month in a locale, explore it to the extent I desire, get to know a few people, learn how the locals live, and then move on.
The foundations of this lifestyle are Around-the-world air tickets from the major carriers [0] and AirBnb. I like the notion of finding friendly AirBnb hosts and learning from them what the local lifestyle is: Where they shop for food, how they get around, what activities they enjoy, what their days are generally like... Then spending a month more or less doing the same things. In the meanwhile, working for pay as a remote consultant.
Total cost of this lifestyle would depend on the class of digs you want to live in. Some cities are really inexpensive, say, Athens or Aukland. You could be comfortable averaging US$125/day for a place and $25/day for food. Another $25 for 'other stuff', entertainment, etc. Call it $175/day, 365/year, throw in the air fare, health insurance and taxes, and you're looking at about $85,000 in income to live this way.
What is interesting is that with this lifestyle, you don't need to own an apartment, or a car, or closets full of clothes. So the money you spend where you are is all the money you need.