My tipping point was frustration with the state of the States. Things have been sliding downhill for too long and a recovery doesn't seem likely. At my age, 42, I didn't think I'd ever see Social Security (unless I lived to the new retirement age of 86). Medical system is almost broken, energy resources are getting fewer and fewer, rights are going down the crapper at a scary pace, water rights are being fought over and rationing happens etc...
I was looking to go elsewhere where any family I might have in the future would have a good future. I came to Costa Rica at the height of the boom four years ago and saw all kinds of opportunities. Met a girl and fell in love. I saw a country that will never run out of water. A country that will have electricity provided by hydroelectric/themoelectic renewable assets. I see a country with the ability to grow enough food. Saw a country where for $50 a month for my entire family, I got all our medical care including perscription drugs, dental etc. for FREE. Saw a country increasing it's industrial base thanks to the crazy import taxes on outside goods. Rest is history and I'm making it and happy with my life here. As for working, that is a complicated story.
What ChiTrekker is talking about is having full permanent residency without restrictions so he is legal to work in any job he can find. In San Jose, there are several $1000+ per month jobs and even more if you have the right skills like computer programing etc...where you can make more. I had several decent offers in the 1-1.5K per month for a bi-lingual resident from the U.S. with a degree in business management. However, therein lies the catch, to live a US middle-upper class lifestyle in San Jose, you would need more than $1000 a month. BUT...If you are content to live a frugal life you can scrape by on $1000 a month but don't expect to be in SL or DR much
Full permanent residency isn't easy to get quickly, usually only through marriage or birth of a Ch*ld (first blood relative). There are some other categories for certain jobs/specialties but but none are quick, meaning you would have to work illegally or have sufficient resources when you come to live for the 1 year to 3 years permanent residency will take to obtain.
However, without the legal right to work, sports-books is an option and know some people who do well and live a good live doing it but know others living in $300 a month apartments and just scraping by with a once a week visit to Calle 6. Working illegally can also be a problem if immigration ever latched on to you, with deportation and restrictions on returning for some period of time.
The last option is starting a business, but again, would need capital to start the business and live until it can provide the revenue stream you need to live the type of life you like. I was lucky in that I had access to enough capital to get a place to live and finance a small business I'm trying to grow into something I can leave the family I have now.
Whatever you do, don't move here thinking it would be easy and without a well thought out plan. That is just a recipe for disaster if you don't have the financial resources already in place.
Hope it helps....