Vanilla do you have an update on your trailer and wiring? I just bought a 2003 Kendon 2 up trailer and want to pull it with my 300C. I noticed your beutiful 100th Anniv. Deuce on the trailer. You mentioned welding and the wiring not going to be easy.
Pulled the trailer from Houston to the Grand Canyon just a couple of months ago. Everything went really well considering what an effort it was to get everything tuned on the trailer.
First, make sure you buy Chryslers hitch, and not the 3 party ones out there. Chryslers is very strong, and is completely hidden. Buy the ball mount adapter, but you probably won't have much use for the ball mount from Chyrsler.
The hitch is fairly easy to install, and can be done in your garage with regular jacks. I did all the work myself. It's a chinese puzzle to get it in there and torqued properly, but it can be done. The exhaust has to be dropped.
The wiring kit for the brakes is not hard to install, but I just felt that a little more forethought by DC would have made it a non-issue. As it stands, you have to drill a 2" hole in the trunk floor and run wires to the battery and the turn signals. The hole could easily have been pre-drilled and capped like the other holes in the trunk floor and it would have been great if a single connector was already there for the wiring (like you often see orphan connectors under car dashes).
Your biggest issue will be getting the right ball height. You need around 22" which is no small feat for a car hitch! You will not be able to use the normal ball mount which gives you like 16 or 17" because you won't be able to load the bikes on the trailer, and you will probably have handling problems anyway.
I bought a 2" ball mount from Kurt with a huge rise, something like 8 or 10". Can't remember off hand the rise.
Your next biggest issue will be slop in the ball mount because you have two 2" shank connections (one for the ball mount adapter from Chrysler, and one for the ball mount adapter itself). With that incredible height of the ball mount, you will have about 4" of slop at the ball itself -- i.e. not good.
For that, I had the trailer shop weld the ball mount and ball mount adapter together. I had them pre-stress it in the up position to get the most ball height.
And then I went to my local airplane hobby shop and bought .025" sheets of copper. I shaped the copper around the shank of the now 1 piece ball mount to effectively make it thicker, and cut out holes for the pin to go through.
Now, I have less than 1/2" of play at the ball....
Your next problem will be the trailer bucking the car as it goes down the road. Probably because of this whole hitch setup, you have more springiness than the regular truck hitch.
Your solution there will be to tighten down the bike to the point where either the suspension is completely bottomed out or the bike frame is bottomed out on some large wood shims. If you fully compress the suspension, make sure the bike is not rubbing on the guide rails for the tires (or you will be sorry later).
Your next problem will be with those super fantastic wheel choks that come with the trailer. I had to remove them. It is such a bear to get the bike out of those choks, that they are not worth it. I use wood shims on the frame to hold the bike up while I strap it down.
You last problem will probably be strapping the bike down. The tie down points on the trailer are not very convenient for many bikes. Just be creative here since I don't know your bike. Make sure you don't stratch or rub off paint on your bike from the straps...
Oh, and you might want to make sure all the screws on the trailer are torqued down properly. I bought mine new, and about 1/4 of the screws were not tightened from the factory...
I put little plastic furniture cushions under the contact points for the diamond plate to stop it from rattling down the road.
And instead of spending $250 for Kendons tool box, I bought a perfectly matching diamond plate tool box from Home Depot for $40 and screwed it to the front of the trailer. Now I can store all my trailer stuff there instead of in the trunk.
I bought locks for the pin, the coupler, the tool box, and also a coupler locker and a wheel boot to deter any thieves that prowl hotel parking lots looking for easy trailer prey. My bike also has a motion detector alarm with pager which is comforting...
Hope that helps...
p.s. My bike is an Anniversary VRod, not Deuce. My brother has a Deuce, and it's a nice bike too...