How much sailing have you done?

Are we talking about a 15-20 footer that can't make any headway to
windward
if
the seas are more than 2 feet, and averages less than 4 knots in ideal

scruddy dood, I personally know a guy with a 19 foot day sailor who has gone CI
to BI and back perhaps as many as a dozen times. I am not sure he remembers
how many times. Ain't no big thing, except to a bathtub sailor.