I can't speak to any lakes near you but I rig my 16 on the trailer every time. To make raising the mast almost effortless, I un-hitch making sure my wheel chocks are still in place and retract the front trailer wheel so the tongue is as close to the ground as possible. This creates a "negative pitch" on the trailer/cat. It's like walking the mast "downhill". Much easier than trying to walk it forward when the tramp has a "positive pitch". I also use a line through a pulley/cleat to pull the forestay while I fasten the bridle. Hope this helps.

Cheers,
Eric