After reading the helpful posts, I think I am ready to proceed. However, I would like to avoid pad eyes if possible (and I just bought a bunch of them and an uber pop rivet gun as well :-/) and minimize the number of holes I need to drill into the boat.
If so, I was thinking, it would be ideal, if I could run the furthest most bow and stern ends of the perimeter lines through the current bow & stern toggle locations. I would then drill a hole through the epoxy filled areas and relocate the toggle points to those locations?
In this way I would really only need to drill two holes (albiet larger holes), and the deck would stay mostly snag free. If this seems like a sound idea, would it be best to drill at option #1 or option #2?