Heading to CR from Oct 14th to the 24th, but only in SJ for Oct. 14th, 15th and coming back on the 23rd. After joining and reading the posts, I knew it was a must to meet up with an experienced CRTer and help make the SJ part of the trip as tiring as the surfing and hiking.

I also hear that "Pops" is well worth the money.
Speak a some Spanish, but by no means fluent. Don't have a problem talking to chicas or really anyone. Laid back and go with the flow.
Downside is, I am staying at the Crowne Plaza, in Sabana Norte, but I had to use those rewards points and don't have a problem dealing with the inconvenience.

Appreciate all the information all the people have posted that have helped me so far!