Oct 2021 I said good bye to a boat that was in the family for 21 years. Countless hours of great times cruising and beer can racing with friends and family. My plan one day is to get a bigger boat for my family and restart the cycle of sailing/cruising/beer can racing. I am a few years away from my anticipated goal to purchase such a boat. However, The Catalina 42 that my father sold 5 years ago is back on the market and the temptation to purchase it "back" is strong. My father took good care of the boat but I will admit, it took some flogging and had been at times ridden hard and put away wet. I took a look at it today and it seems to be almost just the way we left it. 5 more years older, a few things added and taken away. But much of it the same. The port lights look like they may still be leaking (thought we had the fixed prior to the sale in 21'). The bulkhead on the starboard got wet and is discolored and partially rotting. Teak and holly floor in the front stateroom needs to be replaced, and a small list goes on. Not to mention what repairs will naturally need to be done with age. So the question is do I add value for the history I have with the boat, the many harbors I have been to with it and long joyous conversations had over whisky and beer after a great nights sail with friends. Or do I look for a boat that will need less work but no memories attached?