I quickly realized that I really enjoy slow traveling - staying in places for 2-3 months & trying to keep a normal routine. I work full-time now, pretty crazy hours, but I generally move somewhere new every 3 months. I spend a few months of each year in SF & the rest in Europe. I'm heading from SF to Split, Croatia in 3 weeks for most of the summer.
As a final note, there are many different ways to travel. You never really understand how cheap it is until you actually do it. Before I left, everyone told me that I would need a liquid $50k to spend a year in Europe & I remember being worried that I only had about half that - very funny to me now. I've saved more traveling than what I have paying rent somewhere in Australia.
TIPS: * Try & get paid an SFBA salary & live in cities that have a very low cost of living in comparison. * Re trying to get a remote job - move to the job for 3 months first, work your ass off & prove your worth, THEN ask to move remote. * Sell everything. Forget about clothes, shoes, books, records. If you can't pack light at first, believe me, you will learn on the road!