Replying to the note you left a couple years ago below:
A warm welcome from an ex-Boulderite & road cyclist. My wife & I are 18 months away from retirement on a boat. We are heading in the opposite direction from you, the SE / Caribbean; I much prefer the warm water. It's tough being land-locked & trying to get more boat time in. The Hobie sailing on Cherry Creek only goes so far, but it's better than nothing. We try to do mini vacations & combine some boat time with travel. Southwest has some good deals non-stop out of DEN to the east coast. Yachtworld, Sailboatlistings, & sailboatdata are good websites for shopping & comparing different boats.
Just following up to see if you and your wife made it to that sailboat? My wife and I just bought ours, and will be starting the process now of learning to use it well and sail it well, toward living aboard in 2 years.