Rob,
If your trailer is swaying or snaking at 60mph or less, it sounds like the weight at your hitch is probably too low. With my BR20, I use a rough and ready measure - if I can just about lift the hitch off the ground, then it weighs a bit more than 30kg, which is around 5% of the total trailer + boat weight. I haven't had problems with snaking so far (touch wood). For a BC23, if you do yourself a mischief trying to lift the hitch, it's probably about right!
Moving the winch post forward a bit should cure not only the bailer problem but your snaking issues too. I think the lifting effect of over-tightening the winch strap only applies to boats like the BR20 where the bow is quite strongly raked. The BC23's bow looks fairly vertical.