in CR the carib side is definitely rougher in terms of crime etc. seasonal conditions will tell you which side works for you though. your local surf shop may carry a paperback book that is actually a pretty comprehensive guide to CR and other locales...cheap too
I second the costa rica idea. place is absolutely beautiful and there's waves all year there pretty much. another plus is it's really cheap so US dollars will go a lot farther down there. If I ever get enough money to travel there, i'm gone...
My recommendation is the Hawaii of the east coast (Puerto Rico). It's still a US territory so no passport needed and if something goes down you have your rights! Rincon is a great place and odds are you will meet people from the east coast down there if you go in the winter (maybe even some folks from swellinfo). Good choice of waves and DON'T shy away from a reef break. You can get plenty of sandy bottom around here. Reef is one of the main reasons to travel. If you're afraid for your feet just get some 3 mm reef booties and you're golden!
Costa Rica is awesome. I just went for the first time in early August to Nosara. We rented a house - very affordable route if you're not into the whole hotel thing and have a group. Chest to head high waves every day were a 5 minute walk from our house. I think it's a bit more expensive in the winter because that's the dry season there (Nov - Apr). From what I hear it's got pretty consistent swell year round. Very chill atmosphere with super nice locals. Also, the country is just beautiful. Can't wait to get back there.