I had single line on the near 300' main on the Freedom 25 and it worked well, too. Main halyard run aft thru a rope clutch. Ball bearing blocks on hooks made that happen. But I always felt comfortable at the mast and the whole operation took only a couple minutes. On smaller boats I've been able to stand in the companionway and reach the operations.

I would simply never go out without some kind of reefing so it's only the effort to find the easiest way to do it.