I feel I know our local conditions good enough to know when to go out into exposed parts of local bays and harbour.
If anything I tend to err on the side of caution.
I don't enjoy long slow passages riding up over side of a swell or wave and down the other.
Even in a larger boat I tend to get seasick if tossed around too much.
Actually, owning a small boat probably limits me from going out in questionable circumstances that I might take a chance on in a 20 footer and regret later. Also saves me from the wife's wrath...she wants it as calm as a mill pond. ;-)