Ok. I can only help you regarding the wiring a new cable
line in the mast (and pulling it out in the base). Basically, it is similar to what Sailingdog said.
I think it is much easier to drop the cable down than pulling it up. If you pull it up and it gets stuck at some point, you can loose the cable and find yourself just pulling up the messenger
line alone.
So what I did once was:
1. Drop a messenger
line down with a plumb at the end (so it helps it go down).
2. Once it is down (your girl friend can hear the plumb hiting the base of the mast) you prepare a wire with a hook at the end, with a narrow angle, so it can come in and out the small hole in the mast base. More or less the shape is the same as if you take one of those office clips and streighten up all the curves except one (an office clip wouldn't make it, though, because it is too short -I hope I make myself clear and sorry if I don't-).
3. You introduce the wire hook from outside in the base of the mast and try to bring it out with the hooked messenger
line.
4. Then you tie a second messenger
line and pull it up from the top.
5. You attach the actual cable to the second messenger
line at the top. I tie the messenger
line around the cable in a spiral, with a know here and there. And then cover it with tape (not much more than one layer)
6. And you slide the cable down. So from the base you only use the messenger
line to direct and to maintain some tension, not to actually pull the cable.
(Jez, that was a long explanation...)
Good luck!