Ze Plan.

It looks like everything is almost set. I have all the equipment I need(although the thousands of dollars worth of gear will be stolen the moment I step foot into Mexico), and the right tools and resources I feel necessary to ensure my success.
Basically, I think Ive stumbled on enough websites, read enough books, and scoured enough messaging boards now to make sure I don't get chopped up so my loverly kidneys can be sold on the Black Market, or initiated for life into a Guatemalan gang. Ive been reading extensively on hitching, international travel, dangers, kidnappings, routes, street gangs, corrupt police and governments, diseases, do's and don'ts, wildlife, survival techniques, languages, foreign policies etc. Ive been compiling a book together of important resources; think of it as the 'shit hits the fan go-to book'.
Its starting to gather as this; I'm departing from Ottawa, hitching north in Quebec to see a cousin for a few days. I then hitch to Toronto, where I will spend my last two days in Canada for a very long time, with a close friend. I then leave Toronto and Canada, and will chose my USA entry crossing closer to the day. There are several into New York State. Hitching the US should be fun. I will proceed south to NYC, spend a day, then continue to Boston, Philadelphia and further south down the East Coast. I will continue through Myrtle Beach, and eventually into Florida. Its here I will decide if I'm hitching Southwest to rural Mexico. I'm not still 100% on Mexico, as its quite unpredictable. I do have several contacts in the country, and in Mexico City, but if I can avoid early conflict, I will. That being said, I'm almost definitely going to find myself there, so like I mentioned; no plans. If I go from Miami, where I will spend a few days, I will hitch my boat to the Caribbean. I can easily find my way out this way. If not, I can get a boat from Cozumel, Mexico, or continue south through Central America. I have not been, and need to experience this amazing group of countries. I can easily find boats from Panama City, and the canal.(only legal issues a concern here). The original plan was to push south through to the Tiera del Fuego, Chile and Argentina. As much as I want to experience South America on the beginning of the journey, if I plan to attend the World Cup in South Africa, June and July, I will have to potentially cut out this leg. Instead, it will most likely be a boat transfer trip through the Caribbean, and will contain Blue Water sailing here, my first experience. I will then hopefully get my boat to Thailand, or another South Pacific Asian country, as if I go to Australia, they have some strict rules for 'boat people'. These boats I'm referring to are private yachts and sailboats, but I also have the possibility of obtaining work on a cargo ship. Still weighing the options, most likely to be a game-time decision. From Asia, its straight hitchhiking to Africa, although if time becomes an issue, I will cheat and grab a boat from India or something to South Africa.

So....what do you think??