Dude, quit your job and move to Thailand (or some other cheap place) while you work on your web businesses. The cost of living there is super cheap so your daily expenses will be low and your savings will last longer. Plus, you'll get a chance to explore the world. It's not nearly as hard as people think.
Over there, health care in general is super cheap (compared to the USA), and there are plenty of good hospitals/dentists/etc. in Bangkok. I'd bet they're good and cheap in Phuket too. You could probably even pay cash for services like annual dental and vision checkups.
I've signed up with WorldNomads.com for general accident insurance. I've never gotten sick or hurt so I can't personally vouch for the claim process. However, they're recommended by Lonely Planet and a bunch of other notable travel sites. They're worth checking out.
Also you could check out the Lonely Planet message boards too.
Good luck.
Here's a good article that discusses this idea: http://www.expatsoftware.com/articles/2008/05/laid-off-one-t...