Well, my boating has been limited to the 600 acre lake I live on now, so I wouldn't call myself a brave boater at this point... My biggest issue is getting docked in a strong side wind (I can only dock on one side of my dock and I tend to get blown past the dock). It's of course way easier with a helper. I could see this being a big challenge on the broadside of Rattlesnake or Diamond on a W through N wind. The real estate agents showing me properties have had problems docking out there at a few places.
I have a 22 foot Chaparral Sunesta now (from Fay's). If I end up on Rattlesnake, I've thought about getting an additional lightweight boat that I could just pull and leave in the RIA lot when I leave, but that would require leaving the "nice" boat to fend for itself when I'm not around. I hate the thought of paying 2k+ for a slip rental when I plan to pretty much live on the island from May-Sept.
I can deal with the occasional wind by staying put as long as my boat is safe.
I worry more about never seeing the sun on some of those densely treed Rattlesnake lots that face N or NE. It seems like there might be a lot more pleasant May/Sept days if you face S or SW. But then the views aren't as nice and they cost more... No easy solutions.
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