This is not an easy job – it has taken me over 10 years to do it. Most Gringos (Americans and Canadians) give up and go home. Why some people can do this, and some people cannot, is a question no one can answer. But only a few can do it.
When I came here in 2001, my transition was made easier by a fine organization The Association of Residents in Costa Rica (ARCR). Their lawyers helped me though the process of getting my Residency – which was supposed to take 4 months, but took 7 years – and involved bribing an immigration official!
Since then, ARCR has gone downhill badly itself. My advice to anyone thinking of living here is – try it! Getting a tourist visa is automatic, and some North Americans continue to use it indefinitely – leaving the country every three months – or more commonly – getting someone to do this for them where they live – or bribing an official at the border with Nicaragua or Panama. Latino morality is flexible, and considers a certain amount of corruption as natural.
Don’t buy any property here until you are sure you can live here permanently. You can even go back and forth every few months – living up there for awhile, and down here for awhile. If you have the money to do this.
Don’t make any investments down here – you will probably lose everything!