Ebb
I'm not an electrical engineer either but I believe I know enough to handle rewiring Destiny and I'm willing to help you in any way I can.
You said you know that you need "there and back again" when it comes to DC wiring. What is not clear is if you know the "back again" does not need to be a seperate wire for each positive cable going up the mast. You can actually use one single negative cable coming back down the mast for all of the positive cables going up the mast as long as the wire (negative side coming down) is large enough to handle all of the return current of all of the electrical devices on the mast being on at the same time. And here is where LED lights really give you an advantage. For example my mast head all around anchor light is an OGM LED light that draws a whopping .15 amp at 12VDC. That is next to nothing and it comes from the factory with a 20ga pigtail. So the wires going up the mast can be much smaller and lighter if you plan to use LED lights.
So for your example you will need a positive cable for your anchor light, another positive cable for your navigation lights, another for the steaming light and one more for the deck light. That's 4 positive cables and one negative for a total of 5 cables going up the mast. The negative cable just needs to be large enough to handle all of the current going up the 4 positive cables.
Also like you Ebb I'm going to have an Aqua Signal combo steaming and deck illumination light on Destiny's mast. And I know that just above the spreaders is the most common place for this light. However using the CAD software I frequently use and after determining that the deck illumination light was at a 15 degree angle to the mast I was able to determine that to get the light to shine 6 foot in front of the mast (2/3's of the way to the bow) I had to mount it at 7'6" from the top of the mast extrusion. When mounted just above the spreaders the light shines only 4 feet in front of the mast or less than half of the way to the bow's stem head fitting.
For Destiny my mast wiring will go up a PVC conduit (which will also keep the wires from getting tangled in the halyards) so I will use 4 individual cables (I'm currently not planning on nav lights at the top of the mast) bundled together in the conduit. These wires will come out of the bottom of the mast through a hole in my pivoting mast step. The hole in the bottom of the mast step will also allow all water to drain out so none will be left sitting inside the mast to cause corrosion. These wires will feed forward to just behind the forward hatch where they will go through the deck via a Seadog Line 4 pin connector model 426264-1.
My VHF antenna cable will come out of the mast at the same location as the DC wires. To penetrate the deck I'm using a ScanStrut water proof deck seal DS21A-S. This deck seal allows me to pull a cable end up through the deck with the soldered connector in place when I unstep the mast. And while a continuos VHF cable would be the ideal, it just is not practical for me. So I will use a barrel connector just below the deck to connect the mast cable to the cable routed inside the boat for the VHF.
I don't know if any of this helps you with your plans but if not I will try to answer any questions you have. I say "try" because you tend to come up with some pretty good questions.
JERRY CARPENTER - C147
A man can succeed at almost anything for which he has unlimited enthusiam.