what about water balast ?
Even if there is no wind or very little wind having the main sail up will help steady the boat when powering in in choppy water.
I have had a boat with an outboard on the transom and it can get up out of the water, but usually once it digs in and the boat is moving it will stay under. On a trailer boat you most likely are not going to have an inboard although I have seen them on a Com-Pac 20 and I think a Seaward 24 or 26 maybe.
I also have seen websites of people going to the Bahamas in McGregor 26''s. Some of those I would call good at weather windows and some I would call lucky.