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The MacGregor 26D is very simple to set up for a boat of its size. However, it isn't as easy to set up as the smaller boats you have sailed and any additional time setting up means less time sailing on the lake. Getting a slip changes the equation totally. I have mine on a slip at a lake 15 minutes from my house which means I can get 1 1/2 hours of sailing in for a 2 hour window of time. I can also go sleep on the boat even if I have something fairly early the next morning.
Now, I still appreciate the ease of towing and setup of the Mac 26D as I like to take it and explore other bodies of water including Florida. I imagine you would want to explore the gulf and/or some of the other lakes around. I also appreciate the Mac 26D because it has no wood trim on the outside. This means it can easily take staying at a slip with very little maintenance needed. Get a soft bristle broom and give her a scrub every once in a while and you are done.
Forgot to mention, having your boat at a slip means you get to meet other sailors at the marina and possibly even join a club and do some racing, raft-ups, and cruises.
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