Unfortunately we're somewhat trapped in by the slave driver that is money, when you eventually return from travels to settle down, you need to adhere to normal society.
Hopefully the startup will fix that, otherwise I'll just have to do it on the cheap and worry about money later ;)
Ramen Profitable == Beach Profitable
If your service can bring in $500/month, you can pretty much coast indefinitely in a place like Thailand, assuming you completely shut down your life back home. $1000 profit/month will get you to the point where you can travel from place to place. Double that again and you'll actually build your savings while dirtbagging around the world.
My ultimate goal would be to buy a cheapish yacht (they're cheaper than most people think) and sail around the world, like this guy: www.bigoceans.com - once you've got the yacht its not that expensive, I think that would be the ultimate freedom for me, and you can visit places that the average tourist can't get to!
Saying that, any kind of travel is good. I see you live by your word!