Hi Jon nice to meet you
I'm terribly sorry but in the real world of voyaging you are wrong on all accounts. First off if a boat isn't sea worthy enough to handle a little bad weather you shouldn't leave the bay period. You say sometimes which is a very important statement. People who are rushing to beat the dark usually are the ones who make the worst mistakes. Here is a real world example in 6-8 knots of wind on my last sail I raced a 45' ish high performance cruising boat that coasts about 700 grand. I left them in the dust and they eventually dropped sail motored past and asked if I had an electric engine. In the real world my boat is faster than the big ones. I sail rings around large boats in light air all the time. When its really blowing those same big boats drop all sail and motor, I'm not sure why but if they don't have a 2000 mile range their boats are useless for long distance voyaging. So like I said before there are some advantages to larger boats and some to smaller but a sea worthy boat has much more to do with design and construction, followed by seamanship than it does with size. In the real world with proper maintenance and a seasoned skipper there is simply no difference. Then again who do you think pirates will chase, me in my little 22' cutter or the guy in the Halberg Rassey?