Thanks also for that last part, its been weird discussing it with friends/family cause they think its crazy taking the trip without a plan of what I'm going to do after; but that's just something I'll have to live with.
Besides housing and food, do you have any other big expenses? Also, you mentioned you've moved between Indonesia, Philippines and Vietnam, how easy and expensive is it to move around? I'm considering being in Thailand and taking a few weekly trips to visit the surrounding regions.
As for expenses, it depends of your lifestyle of course but it should cost $25/day for basic expenses (housing + food + beers) . If you want to travel around it will cost more. Also language courses you have to pay, yoga classes etc. But everything is much cheaper. I go to a salsa class here and it's $2.5 for 1 1/2 hour.
There are lots of cheap flights between countries, check Air Asia or Cebu Pacific Air for Philippines. Or from Thailand, you can take the bus/train to Laos/Cambodia.
Thailand is more expensive than Vietnam, although it's still much cheaper than most western countries.
- I made sure somebody would take care of my incoming mail at home. Also make sure your financial situation,tax etc is handled.
- learning the local language + spending time on your own stuff sounds awesome
- 3 months for $5000 should be definitely doable. Renting an apartment beats moving around from hotel to hotel, however you might be interested in checking the country too :-) Mostly, avoid restaurants that serve western food and touristy neighborhoods, as your money will not go far there.
- doing web dev work would help you keep up to date. You can also see whether locals need help with their website/design needs (for example hotels, travel agencies etc.)
Relax. I know it sounds daunting when you're at home, but it's really not as dangerous or complex as people say. Don't forget to pack light. I have a 35-liter backpack and that's been enough for 5 months traveling/living in SE Asia, including laptop for work :-)