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I'm no expert, but my husband and I have been doing a lot of research prior to our relocation to CR, and it's my understanding that $1000 a month IS a lot of money by Costa Rican standards.  I've been told that the average median salary by a CR citizen is $900 per month. 

Now please don't rely on this info, it's just something I've read by searching online. You can do a google search on the average income of the country, that's where I found this information.

Good luck with your research.

Yeah, I guess I should have said a little more.  I'm sure you're correct about the average salary.  But to support a wife and child, and maybe another coming at some point... plus being able to fly back to the U.S. maybe once a year... It starts to add up quickly.  I think somewhere in the $1500-$2000 per month range would work, but for me I think $1000 would not be enough.

Keep in mind that for almost all jobs you must have your permanent residency.  There are a few exceptions.

Oh yes, I'm aware of that too.  As I understand it, you have to have a sponsor who will say you can fill a job that a citizen cannot fill.  So teaching at an American-style school fits that bill, as I understand it.  But there aren't too many other options.  So yeah, it's a tough thing to figure out.  The best I'm left with is trying to work online.  That's basically my only option.

I wish I could offer more help, but I'm about lost because everything is so new to me. 

I wish you well, Lollard and pray you will find your way to success.  Please, if you find time, keep us posted on how things are working out for you. 

Yes with a family and wanting decent housing, you will need more than $1,000 a month in my opinion.  It is less expensive there for some things and actually more expensive for some.  Like pharmacy stuff is more expensive than the US. I would see if there are any big American companies that are down there already, and I hear there are quite a few and see if they have any openings you can do as I'm sure they pay better

Lollard,

Living with a $1000 USD a month in Costa Rica is difficult specially if you have family. You can do it, but you will need to give up a lot. You will need to rely on public healthcare, public education for your kids, cheap unhealthy food, you get the picture.
Teaching English is not what it used to be. There are so many expats living here that it lowers the wages for English teaching positions.
Look at elempleo[dot]com. Maybe you will be able to find something that suits your needs there. You can also try indeed[dot]com.
What TerrynViv tells you is somewhat true. Although you are not required to have permanent residence, it is certainly required to have some sort of status. Please note that there are dozens of categories available under the immigration law of Costa Rica. There is also a category available for entrepreneurs who have their own business. By the way, there is a category you did not mention in your initial list, the pioneers. The working families that are just looking for shining city on a hill.

Considering LOW rental costa and Utilities $100,000 is consider a GOOD wage for CR !
REALLY I manage a 3 acre property with 3 houses and 3 apartments overhead for LESS than that

oops then if you live above THAT salary like a New Yorker I am sorry to say MANY families survive on MUCH less ..but you will NOT love CR I guess

only thing is NOT everywhere NOT in our area is the food UNHEALTHY
We have Sunday Farmers Mkts and GOOD healthy CHEAP little cafes ,,Got to FIND them and stay away from Gringo Gulches where they DO gouge the Gringos who are USED to paying more ..IN 22 years Not gone much more expensive and GREAT restaurants here in Central Valley...

TRUE Laura !!! $1000 some would give their eye teeth for,,,

HAHA ..NOT $100.000.But $1000 .I was  wishful thinking !

Most of us live here for the weather, the people ,the Natural  beauty. and the Entrepreneur opportunities and we Forget about the Almighty Dollars we earned in places like New york and Hollyweird..pura Vida AND  hard work kept me here 22 years ....

REMEMBER UNLIKE 22 years ago ..there are NOW MANY Ticos who speak perfect English to fill those jubs..I know several who are working for Us companies here and bi Lingual BUT not earning $1000 in a 3rd world country...

When you have an influx of Expats relocating to a country such as CR, how does that really help the economy or the people when you have so many of them driving up the cost of real estate with their unbelievable demands for luxury housing and so many modern, (especially american) conveniences and isolating themselves from the locals.

as someone mentioned "There are so many expats living here that it lowers the wages for English teaching positions"...Really??

Hello  I cam here at age 37   20 years ago.  I have never had a job that paid $1000 a month in all those 20 years, the most I ever made was $800.  I have 7 years of university and speak almost perfect Spanish.

20 years ago I fit category 3  Young single no family and able to live on almost nothing anywhere.  And that is what I did for 4 or 5 years until I got things working.  If I had come here with a dependent wife and kids  we would have starved  and literally as there is no welfare of any kind except subsidized medical  of poor to médium quality.  I lived in $100 a month roach rooms and ate beans and rice.  I did have the good fortune to come with $13k cash which is what kept me here while I worked
my way through the system.  W/o that 13k i would have been here 1 month max.

Right now that $13k is like  $50k  so if you have that you might want to give it a try.

Certified teachers at private schools don't usually teach English...they teach multiple subjects in English.
Teaching at a language institute with only a TEFL or TESOL diploma, would possibly earn you half of your $1000 and you would be expected to work evenings and weekends. They very seldom are on the up'n'up' and often do not pay your CAJA which they should do, by law.
Plus to get a work visa the employer must apply for it, not you. And if you quit or are fired you visa is no longer valid. Nor can you, legally, look for extra  extra 'work' elsewhere in your 'off hours'.

There are many more rich Ticos than there are rich Gringos Most of the luxury homes are owned by Costa Ricans and there are huge tracts of land that are owned and operated by Tico families. Most of the homes in gated communities are owned by CR citizens, and yes, they own more more expensive cars than 'we' do.
Weextranjeros are in the minority here.