I trailer sterns first, too. In fact, many sailors here do it (note the photo). Catman solos up his Mystere 6.0 mast this way. It lets you solo-step very quickly. Here's a photo of me doing the dead lift, starting by sliding the mast forward a few feet onto the step, then lifting from the ~30 degree angle of the mast on the trailer mast crutch. If you can park on a slight beach grade the mast ends up leaning against the side stays with gravity holding it forward. I pull the forestay tight in my hand and step forward to clip it to the bridle. Takes about 10 minutes from keys off to mast up, always solo.

Note my trailer balance. Unlike Alan's Nacra 5.5 photo, my trailer's cross beams support the boat nicely, even with my short trailer. It takes a few adjustments from a bows forward rig but you'll never go back to the old way.

Loading and unloading from the trailer is easy, too. With CatTrax there is no lifting at all, everything solo. It's all about balance.