There is no trick
You do not state which boat you have but from your post I assume it is an S. I got a 100ft reel of 14 gauge marine wire from boatfix for ~$60 and that was enough to rewire the whole boat. The only problem was the bow light and stern lights. Like you said the wires are pinched between the three hull sections. There is nothing you can really do. I ran three new lines to the stern (pump, running and anchor light) and ended up splicing into the existing bow wire as high up as possible. I used the crimp connectors but got the ones that are filled with wax and use shrink tubing. So when you heat them they seal water tight. I guess if you want you can run a new line to the bow light after drilling holes through the inner hull but I did not bother. I like how the newer S's are run with the light in the bow railing, mine is on the hull... So just do any way you can. There is no trick.good luck,mark