Interesting point. I had a similar situation one of the first times I went sailing. I took the trailer straps off the hulls before raising the mast. When I leaned forward to attach the forestay, the boat tipped forward about 35 degrees until the hulls hit the ground. It was much easier to attach the forestay, but I felt like an idiot.
My thoughts on your procedure are as follows. If you trailer your boat facing forward, then you have to rotate it about 180 degrees to get it to face downhill, toward the water. Then you have to turn the boat into the wind to raise the sail(s). My boat weighs 390 pounds and is quite difficult to throw around, even with two people. This seems like a lot of work, much less than just using a set of lines. Do you use Cat Trax or something? Can they be used to develop the proper incline without all the turning? Do they facilitate the turning? I haven't used mine yet, so admittedly have no experience.
Caution: Soapbox Alert!
Yes, I agree, it's much more safe and enjoyable to have a second person there to assist. However, as many of us know, getting someone to go sailing with us as often as we'd like is not always easy. There are times when you just have to go sailing, even if no one else does. This discussion is for those times. Last weekend, I went sailing with a woman that weighs just over 100 pounds. How likely do you think she would be to help me in the very physical procedure of raising the mast? I used to never go sailing without someone else. I thought that experiences like that should be shared to increase the appreciation. However, after a breakup, I had to singlehand often. At first, it detracted from the experience, but later, as I got over myself, I came to realize that singlehanding can allow you time for quiet contemplation, without external distractions, other than actually sailing the boat. This becomes a pure endeavor, and a classic example of man against nature, or more importantly man in harmony with nature. I think that one of the main reasons sailing has survived the industrial age is that it is a pure example of man harnessing nature and putting it to his own use, but one of the rare examples where nature isn't lessened by it. Sorry, but I warned you.