For every degree the boat is pointed downhill, there's one less degree you have to raise the mast toward vertical, so it will help, but making "gravity work in your favour" is a bit of an overstatement. I'm rather short, and, when the mast is in that difficult zone about shoulder high, it's still not far up, and I'm closer to the pivot point than a lot of folks. I much prefer to have the boat pointed downhill some...every little bit helps!
That said, you still need someone or something to hold the mast up while you the forestay is pinned. (We have a guy in our club who will raise the mast and hold tension on the forestay while he jumps down and pins it. He does a lot of other disastrously dumb stuff, too.) If you're raising solo, using the jib halyard as described above is the way to go. I run a cheater line from the halyard around the front of the bridles, and through the jib cleat with the bitter end in my pocket. The cheater, trap wires, and shrouds need to be laid out nice and clean so they don't foul, trip you, etc. during the process. Once the mast is up, you tighten the cheater securely in the jib cleat and pin the forestay. For me, it also helps if the head end of the mast is resting on a ladder or such (mast is not resting on the rear crossbar) before I start.
_________________ Jerome Vaughan Hobie 16
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