I've given a lot of thought and research over the past few years to a practical approach to "sea-steading" or living out at sea catching seafood and gathering seasonal fruit from the shore, but as beautiful and full of food as the sea is, I found out from spending time on and near the sea in various countries that it doesn't suit me for long-term living and I am a land lubber. However it would be great to see others making it work. I suppose I'll always prefer the ship of the desert (dromedary camel) to the ship of the sea. I've always enjoyed Heyerdahl's books about his sailing primitive vessels across the oceans and living more traditionally on the sea.
One of the things I found out is that unless you know how to build a large enough boat cheaply and you have experience fixing boats and so on, you are going to have a tough time dealing with all the expenses of purchasing and maintaining a boat as the initial costs can be quite expensive, not to mention dealing with alot of hassles if you plan on moving through international waters, and from what I have heard you will have a tough time crossing oceans without a large enough boat. It can be done, but I've heard of many stories with people who don't take these tidbits into account and end up losing a lot of money because they weren't prepared for all the time, expense and work involved. Also many people sell defective boats and unless you know what to look for in a boat you could end up with no money and a rickety vessel that won't take you very far. Especially with catamarans there is a lot of junk out there that you don't always notice during the sale.
I heard about some people who have pretty much left the U.S. or Europe for good and are living on their boats near islands in the south Pacific, however they still have jobs (whether fixing boats or electrician work, etc) to help with expenses and they gather fruit seasonally from islands and grow some vegetables on board their ship and fish to supply most of their protein. Most of them are rich and have quite a bit of money to pay for their boat and other associated expenses that come with living on the ship.
However, I also found out that if you can make the right contacts, you can make things more inexpensive and get some practical experience that will help you later on. Contacting boat owners and offering your services in exchange for travelling on a yacht or other vessel would definitely help when looking for a cheaper boat, learning how to fix and maintain boats and acquiring the proper skills needed for living at sea and finding work on boats. I know of people who do this and have travelled all over the oceans from place to place without spending much money at all.
I wonder if perhaps some coastal parts of Asia might be more practical money-wise than America for living on a boat where there is more availability of different kinds of vessels and cheaper start-up costs, and more of a boat-living culture with the local people to make things go a bit smoother.
A few books that may interest you:
Sea-steading by Jerome Fitzgerald
Sailing the Farm: A Survival Guide to Homesteading on the Ocean by Ken Neumeyer
Voyaging on a small income by Annie Hill
In any case I would be interested in hearing your plans regarding this grog.