Size
I spent the whole year up on Winni in a 20'er. I both agree and disagree with secondcurve. I intentionally went for a 20 because I wanted something easy to tow and easy to manuver. There were definitely days where the ride was what I would call "active", but slowing down and having patience, I was still able to go everywhere on the lake, any day and any time I wanted to. I never felt unsafe or out of control even on the worst days I was out (and I was out there with the wife, 7 year old and 4 - 8 month old). That said, the Cobalt I bought was just about the heaviest and most solid (IMHO) 20' I could find and that is what drove my purchase. Plus, I could almost always find enough dock space to shoehorn a 20' boat in...
That said, when I saw the great opportunity for a 24', I went for it. Longer boat, heavier and a better ride because of it. I like to cruise around 30mph and wanted that to be a little less weather/conditions dependant...
So, I dunno, I suppose I think that it all leads to expectations. In a 20', expect to slow down, take it easy and plan to limit your distance on the worst of days (and find ways around the Governors/Weirs/Meredith area.
I put 61.5 hours on my 20' and had the best summer of my life. So, I really think it's about being realistic and setting expectations about what you will want/won't want to do.
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