3-5 year RTW finacial planning 101?

[wildlands1]

OK, the farkles on my '09 wee-strom are almost done. The divorce is soon final. ($$$) and the old dog will be dead within 6-9 months() so soon begins the money part.
I'm thinking $75usd/day average total, including shipping, = $525/week, =$2250/month,=$27,300/year. Heck, thats cheaper than staying in USA. I'm gonna pack all my remaining stuff in the shed and rent out my house, sell my cars, and anything else possible. In '03-'04 i averaged $66usd/day for a year around CA/SA solo from USA, but I wasted so much money on latinas. Now i (mite) know better?
5 nites a week cheap hotel @ $25/nite = $125/week (more in some countries, less in most ill spend time in, camp sometimes also)
Food, $5/meal (road food or cook some)= $15/day, = $105/week
Beer & Cigars $10/day (or less?) = $70/week
Petrol, 4 tanks/ week @ $5/gallon = $100/week (i ride short n slow)
= $400/week. = $125 saved for girls, shipping, scuba diving, park fee's, visa's, etc..
My first big expense will be trans pacific shipping to somewhere across, maybe NZ, or OZ, since to the philipines, my first choice, looks impossible (why?) and scuba diving in SE Asia. Once thats done itll be much cheaper i think. I know from past experience based on my frugal travel style that Viet/Camb/Nepal/India will be way cheaper, enabling my budget to bulk up for more pricey areas down the road. I dont plan on having any health insurance from USA, if something happens, ill suck more out of my retirement i guess. Anyone with recent travel experience have any advice?