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I own a 1983 Mac 25. Had it for two years now. The first year I dry sailed it, one hour to the lake. Took me and friends about 40-60 minutes to rig and unrig, launch and retrieve. It is a huge pain in the azz, I can tell you, and thus I put it into a slip this past summer. If you have the financial wherewithal to slip it, or at least store it at the marina with mast up, I would do it. This way you can sail any time, not needing a block of several hours in order to get a two-hour sail in. You can go after work, or any afternoon, etc. You will sail a lot more if you have a slip because you will not need as much time, and will not have to go through the PITA every time you want to sail. The PITA discourages one from sailing IMHO. Definitely go with the slip if possible, or storing mast up if slip is not possible. Trailering to and fro each time you want to sail will mean less enjoyment because you will not sail nearly as much. Trust me.
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