almost all the regular sailors where i sail trailer our cats that way (sterns towards the car) so we can use the yoke of the mast to support and kick start the lifting
we all have 30 and 31' masts and solo step all the time.
I personally back my trailer down the shoreline till the boat is on a slope to take advantage (just like a tilt trailer does)
This image is where i leave the boat to rig it. after everything is set.. a back it down the slope till the wheels touch (or the mast is at a good angle to assist in the step)
Edited by MN3 on Jul 10, 2013 - 04:33 PM.