Well Gary, I'm lookin at it thru Neuevo Hillareah eyes, formerly NY, and I really can't comment on the corrosiveness of Indiana air, but here, we get all the downwind contamination from the rest of the country, so we do a lot of rewiring on equipment. I can strip insulation off the wire in a 6 month old truck and the wire will be green.
On top of that, any wire you run under a truck will ABSOLUTELY find every sharp spot on and along the frame, and chew insulation off on that sharp spot.
I've got a pretty good idea what you're trying to accomplish, one of my buddys has a winch setup that plugs into his receiver, and then he hauls the trailer from the back end of the winch. (I'm not going to comment on the dynamics of that setup)
A lot of experience with electric winches has convinced me the clocer they are to the battery they are operating from, the better they pull. Most winches suck more current than a starting motor on a big block, and do it for longer.
I set one up on my car trailer 20 years back that had 3/0 welding cable running from the battery to the winch, and it didn't run worth crap. I added a battery onto the toung of the trailer, and the winch performence doubled.
There are a lot of questions you need to answer before you set something like this up.
1) How often will you change towing trucks?
2) Will you tow with multiple trucks?
3) how far do you go out before you use the winch (charging)?
4) How often will you use the winch?
5) How regularly will you use the winch without the trailer?
6) How long will you keep the truck after you go thru all the setup?
7) Is there an easier/ cheaper/ more useful way to do it?
If you do run any kind of heavy cable along a truck frame, pull it thru an old hose for protection, and have a disconnect as close to the battery as possible.
Since you already have a battery on the trailer for the hydraulic pump, how are you charging that one? Wouldn't a long set of jumper cables (plug in type) be more cost effective?
If you know a forkilft dealer you can generally get battery plugs free from junk batterys.