Costa Rica is nice....it's the ride through the country's between here and there that can cause the problems. We had a USCRA member that had his wife murdered on a ride through Mexico a few years back. Recently had a friend that was going to drive down to CR with his tools...he's a carpenter. We finally convinced him to fly down and have his tools shipped. I don't think he would have gotten there with all his belonging intact. Half the roads in Mexico are on the AAA list of roads to avoid due to the danger of being a victim of crime.
Short of riding through the southern half of Africa it's probably one of the most dangerous corridors of travel for lone travelers. At least that's what I've heard, never done it myself. Lots of beautiful places to go in the US and Canada....hard decision to undo when you are alone on a road in Nicaragua with your bike and wife dissappearing down the road in the back of a truck.
I know people that live in Costa Rica and have been back and forth to the US dozens of times....and have never driven...and never would.
JohnnyB