Travel gear / packing
I've traveled by motorcycle for the last 1.5 years in New Zealand with no saddlebags, tank bags, etc. Everything has been strapped to my body… this is much easier with less stuff but can be done with all camping gear, clothing and even traps for catching possum!
Visas & immigration
Visas depend on your country but Americans do have it pretty good. Working holiday visas and regular visas are pretty available. As far as setting up a bank account and getting a tax number – don't waste your money on a program, this stuff is not that complicated.
I've been abroad for 2.5 years straight. I started with $12k student debt and no savings – I put my plane ticket on my credit card and went to Australia for a working holiday. During the last couple years I've paid off all my debt and put some money in the bank while working in progressively better jobs. I've lived and worked in Milford Sound and am currently back at the ski resort for another season with free room/board, ski pass and gear!
I don't travel with others – it takes more time, money and you don't even get to do what you want half the time. The opportunities available to solo travelers are incredible.
During my travels I've learned valuable lessons about not just making money, but keeping it. Making a good budget-friendly plan starts with booking flights and ends with what you eat. I've developed a diet which allows me to live in New Zealand on $10-20 a week (would be less in the US) which includes vehicle fuel and accommodation. It's not luxury but most backpackers will go to further extremes to save what I do.
I lived/worked in Australia for a year and I've been living/working in New Zealand for the last year and a half.
I'm from the US and have traveled across the South and up the East Coast.
I've been to Greece, Netherlands, Ireland, Scotland, England, France, Spain and Germany.