I've done my dreaming about being "homeless and unemployed". However, unlike the thread heading of "no assets", I'd like to do it with $ in the bank and ability to cover things like health issues (either via insurance or payment).
I also resonate with the minimalist approach of fewer possessions. So far I've taken two long cycle touring vacations of a year in 2001 and ten months in 2007. I'm already dreaming of another long trip (~6 months to ~2.5 years) in 2013. For each of my previous long trips, I decluttered both prior to the trip and also afterwards. Spending a year on the road gave me a new perspective on all those possessions I owned but hadn't used in the preceding 12 months.