No worries GamTrak, pretty much everyone speaks english, especially in the populated areas like San Jose. It is their second language, so if you know a few basic words of spanish, you will be fine. Plan on taking taxis when you are in San Jose, they are extremely cheap — like 2-3 bucks to get anywhere in the city pretty much. There are no addresses BTW, so you will have to know the places you are going too, and it is helpful to know a major landmark near less popular places.
You don’t need to worry about converting your dollars into colones as most everyone will take american dollars, you get the best conversion rates by putting money down on the casino tables, unless you loose it gambling of course. Have fun and make it out to Jaco if your are looking for good time on the beach. I would recommend the Copa Cabana as a decent place to stay, it’s right on the main beach.
Unfortunately, I won’t be able to make it to the show, maybe one of my business partners will though.