You can have the best of both worlds. I started working (iOS consulting) and travelling two months ago and I save more of my earnings here than I did living in San Francisco. Today I signed a lease to rent a shared house in northern Thailand and my rent is $160/month for a place that would cost a small fortune at home.
I found that constantly being on the move is difficult to keep up for weeks at a time. So now I have a base from which to explore the surrounding countries.
There's a surprising number of expat tech workers in the city (Chiang Mai) but now I can sit in a cafe without overhearing social-local-mobile startup pitches.
I can't see this being a problem in most places. Most places will be a small deposit plus a month up front in places in Asia, Central America etc, however more developed places such as London, Syndey etc will be less tolerant / desperate for bookings.
The two most useful tools I've found when doing this is Tripadvisor and Airbnb, you can usually haggle a room from either of these longer term.
Most landlords here will let you lease a place for 6 months as a minimum. Most have no problem with renting to foreigners. I had to pay a deposit of two months rent and one month rent in advance.
If possible try to avoid English-speaking property agents as they charge a premium. The best approach, at least in this country, is to drive around with a native speaker and spot 'For rent' signs.
Yep, a double entry tourist visa. It's probably the largest drawback of being here as I have to leave the country after three months and come back; this literally involves taking a bus to the Burma/Laos border, walking across a bridge then walking straight back to the bus.
There are ways round it though. If you take a 'Learn Thai' course at an accredited institution you get a year long visa. A little more expensive though.
I found that constantly being on the move is difficult to keep up for weeks at a time. So now I have a base from which to explore the surrounding countries.
There's a surprising number of expat tech workers in the city (Chiang Mai) but now I can sit in a cafe without overhearing social-local-mobile startup pitches.