The jobs that are the most in-demand for expats in Costa Rica

There really is not much demand for expats to work in Costa Rica. Perhaps some Americans to be English teachers, but that's about it and probably not very much of that.

Of course it is basically illegal for a gringo to work here, except if a company needs your unique skill and is willing to do all the paperwork to hire you. Which is rare if not unheard of.

Basically if you need to work in order to live in Costa Rica your only real option is to work online with your base of operations in the U.S.. For example you could sell advertising or books or products made and sold in the U.S. via the web. That is perfectly fine, but it's not easy to make money online and don't fall for all those ads saying how if you buy their "system" for $200 or whatever they'll turn you into a rich internet entrepreneur overnight.

In my experience, most people come here to open up their own business, usually a restaurant.  As a non-resident, you're not allowed to work in the business, but that's a law that is constantly being broken.  Within a year or so, the business is usually up for sale so that somebody else can give it a kick of the can.   If you plan to come here to make a living, don't invest more than you can afford to lose, in my opinion.

Working in cr requires residency, free of restrictions, even at call centers. Working at home, can be done, if the money goes into a us account, otherwise the local banks will require proof of origin, and then there's the issue of taxes. Some just do their thing, and that's ok,,,, until you get caught. Fines are high, and one can be expelled and barred from returning for a decade,,, SO be carful you all.