Sailing fun outweighs resale
Unless you expect to race, forget about resale on a Daysailor. I have had an O'Day Rhodes 19 for 20 years and wouldn't consider replacing it. The entertainment it has provided has been the most important value. As I became confortable sailing it, I replaced things such as sails, kicker and trailer and even had it repainted. The money you will spend both enjoying it and maintaining it over time will far surpass any difference in resale value. To have total strangers walk up to me at the launching ramp and say, Wow! I used to have one like that. Wish I still did. Well, every time I head out into Galveston Bay, I smile.