Richard--
I stepped my F27 mast on and off the trailer depending on the situation and it felt very manageable in both scenarios.
Jim Love did not build Undaunted with trailer stepping in mind, although some 31-33 models do so. It has no trailer winch nor bow guides. With the heavier and taller mast, I enjoy the stability of unfolding first, as well as the safety zone of the nets/floats. The downside would be if it were launched at a location with boat wake or waves, which isn't an issue for me.
You'll find a treasure trove of debates regarding this in the Fboat forum but it's more or less 'to each their own', the specifics of the location, the boat, and the preference of which variables the owner decides creates the greatest safety margins.
You're welcome to come watch a water stepping on the 28th!
Ginnie Jo