I was there for 2 weeks in November..
The roads aren't as bad as they're usually advertised to be - the main roads are in fairly good shape - so highways and the big routes from city to city are in good shape. Those roads are being shared by horses, cars, tractor trailers, cyclists, and pedestrians, though. There are a ton of cyclists everywhere and people are generally pretty good about cyclists (we rented a car and drove for the 2 weeks)... I will say that costa rican drivers only seem to pass people on roads when there's a blind turn or something like that.
There are a lot of people riding around in like full racing kit (spandex tights & matching shirts) on mountain bikes or something similarily incongruous.
Here's pics that I took of cyclists when I was there:
If you go out to the main directory you'll see more photo directories with costa rica pictures - I think you should take up kayaking if you move down there as well
And rent rooms to me so that I can go down there and stay.
I did see a lot of americans living in gated mansion type communities isolated from the people of Costa Rica - who'd been living down there for 12 years and could barely speak Spanish - so I'd say... please don't be one of those! That's just sad.
If you ask about specific areas of the country, I can tell you what I know about those - they do have a long rainy season, so if you want to avoid that - maybe move to the north west type area. the more rural you get, the worse the roads get though.