Think of it like this ShinneryOak, if your lower limb is going to be under more stress when you're actually shooting the bow then your tillering board method should reflect that as close as possible. I know this goes against conventional wisdom ,but don't you think by moving your string hook down to the other side of your handle that this would more closely match your hand drawn profile?
Personally, I don't set my tiller on the tree. Rather I start just as soon as I can get a short string on and feel my way back to my intended draw length. Using the proper grip for my layout I'm looking for evenly strained limbs at full draw. This in itself will set the proper positive tiller I will need. If I had to do this just on the tillering tree then I must know (by measuring each side of the fades) just how much positive tiller to add for good long term tiller health. That comes from experience............Art