Are 27s trailerable?
While you occasionally see 27 foot boats on trailers, I question how practical this really is for other than seasonal launching and storage. Keep in mind too that both the O'day 27 and 272 have a 9 foot beam, 6 inches wider than the legal maximum for trailering without a permit in most states. There is a difference between "trailerable" and "transportable". If you want to trailersail on a regular basis, I think you'd be happiest, and sail more often, with something a bit smaller.