The latter is the better option right now and it’s been trending up for a solid 7-8 years and will continue due to the mere reputation, location (San Jose is land locked), and weather. There are two main hot spots for prostitution in Costa Rica: San Jose, and Playa Jaco. I’ve been numerous times with my buddies, and even took sabbaticals from crazy New York City to enjoy the life they call “pura vida” down in the Central Valley of Costa Rica, finding flings along the way.
While I don’t know the history of the paid sex down there prior to the year 2000, I can give you an idea of what it’s been like the last 19 years. This is a topic that’s gone so mainstream that a South Park episode was dedicated to this exact topic. What’s the Deal With Sex and Hookers in Costa Rica?