To add to that when I first bought my Island house I was also, obviously, in the market for a boat. I began my search looking at 21 footers. While doing that I noticed a substantial difference from 21-23. Things that made a big difference in terms of staying dry in rough water. If you have the dock space I am suggesting you bump up to 23 feet. I just feel like that is the magic number on Winni in terms of a boat that will be able to handle most of the conditions on the lake. Of course you may be limited by your mainland dock space so this point could be moot.
As for brand name. The old adage you get what you pay for often applies in boating. Not all the time but most of the time. Names like Cobalt, Monterey, Sea Ray command higher prices and they are well built boats. With that said a few of my neighbors swear by Four Winns and you know what? For the money they make a hell of a good boat. Another name to consider is Chapparal. I think it is probably going to come down to money and personal preference. Most of the big name 21-23 footers will suit you well. Good Luck in your search.
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