Re: The economics of sailing around the world
When circumnavigated in the 70's I estimated our personal costs at about US$100.00 per person. Insurance wasn't even something one would consider at 1/4 of the value of the boat per year. There were lots of places where a haul out was quite reasonable or free (pilings on a beach). Decent bottom paint could be had for about US$100.00 for 5 gallons from a ship and sails were built to last, unlike the 5 year/100,000 mile "guaranty" of today's sailmakers.
There were not too many expensive electronic aids to break; sextants, stop watches a radio or 2, plotting sheets and a taffrail log, were about it, and not too perishable.
I believe today a couple could cruise comfortably on about a grand a month, but you aren't going to be eating prime rib too many times a month. Keeping damage and wear and tear to a minimum by sailing conservatively and doing haul outs in third world countries would help a lot.
You won't get insurance in that, personal or boat, and things like the Panama and/or Suez canals would probably require a bit of skimping for a few months.
My best suggestion is to get an annuity which would pay you a fixed sum each month, so you know exactly how much income you have each month. Split it into two accounts; one for expenses and one for emergencies.
Working in foreign countries is pretty much prohibited unless you have a skill which they do not, so you can either work for other other yachts or do deliveries to augment your cruising budget. Chartering for cruisers is a pipe dream.
Buying provisions in bulk, if you have the room, can help a lot, but it restricts variety and some folks just can't handle that. Canned butter, cheese, whole chickens and cabin biscuits are good staples and many of the SoPac islands have very reasonable Red Chinese foods in cans.
Always make friends with the crews of freighters; they have washers/driers aboard, free cancelled charts and you'll probably be invited for a meal and a few drinks in their onboard pubs and a game of darts, if it's not a US ship.
But if you can't "live like a local" food wise, it will be very hard to do a trip for that kind of money.
"Any idiot can make a boat go; it takes a sailor to stop one." Spike Africa aboard the schooner Wanderer in Sausalito, Ca. 1964.