I got back into astronomy in 1986, after a 15 year school hiatus – my interest sparked by the reappearance of Halley’s Comet. The next 20 years were filled with fantastic trips to star parties and astroimaging safaris far and near. The vast bulk of these trips were to extremely remote locations that were dark and clear – places that my family had no interest in visiting. I dreamed of building another observatory in a site that was dark, accessible, safe, and family-friendly which would house a larger, non-portable telescope to do serious deep sky imaging. Living in southern Florida, the Chiefland Astronomy Village (29 deg N) in northern Florida fit the bill perfectly. The Chiefland site is blessed with dark Bortle 3 skies which are steady thanks to the influence of the nearby eastern Gulf of Mexico. Most importantly is the fact that my family bought into monthly visits to the village, now accounting for over 100 visits to date since the observatory was built in Fall 2007. The elevated roll-off-roof observatory we built was designed by astroimaging czar, Barry Riu. The observatory houses an RCOS 14.5″ f/9 ion-milled Ritchey-Chretien telescope on an Astro-Physics 1200 mount with Apogee U16M CCD camera, with adjacent warm room. Barry Riu roboticized the observatory in 2010 so it can be operated from remote sites, such as southern Florida or even underwater. This experience has far exceeded our expectations for a dark sky astronomy site, filled with camaraderie, learning, and exchange.