Lately I was considering settling down a bit. However, I am pretty sure if somebody comes offering me a job in Patagonia, Chile or similar I would live tomorrow. As the OP says, it weights more on others than you, you get used to it at some point. The only real problem is rebooting your social life every time, especially if you end up in a small city: if you are introvert, you need to get a hell out of your comfort zone to make this work.
Anyway, my question to the OP: how did you do this financially? I mean, were you always able to get into a good position and keep building up savings? If so, was this due to your technical skills, networking or other? I am asking because in my line of work (finance-controlling) having manual work in the CV would be quite detrimental.