As both a sailing and a flying instructor I deal with these issues
quite a bit. You don't want people doing stupid macho stunts and
killing themselves, but there is also such a thing as being too
chicken. Beyond a certain limit you have to wonder at a person's basic
ability. A pilot with little short field experience passing up a 1200
foot strip is a smart pilot. If he is unsure of getting a Skyhawk into
a 2500 fot strip then I would wonder if he had the required aircraft
control skills to be flying AT ALL. You can sit in "chicken harbour"
because you aren't in a hurry, have been in storms and bad weather
before, and would like a relaxing trip. If you are waiting because you
are unsure of being able to handle anything but the calmest weather
you are accident waiting to happen. Forecasts are not perfect and you
WILL be caught out sooner or later. Iknew a guy who passed on going
to the Bahamas in a large trawler because they didn't get a weather
window in 4 MONTHS! I can't imagine there was weather THAT bad for
that long in Florida.