The wire is a mil spec (usually prestolite) 14 gauge wire. It is a very high quality wire, as evidenced by it's losing it's installation now, after just 60 years. It is available from many of the jeep supply guys, I believe John has it at midwest, and I'm pretty sure Brian Asbury has it up here. Shell out the money and buy a good length of it. You would be hard pressed to find better wire anywhere else, and it is the only correct wire for M-series vehicles.
Re the contact for the light bulb, yours appears to be a small washer soldered onto the end of the wire. You can renew it with some fresh solder. You could also replace the wire at the same time, once you get the right stuff.
Re the two upper bolbs, the smaller (#623) bulb is for the running lights (should be wire number 21 powering it) while the larger (#1251) bulb is for the brake light (and turn signal if so equipped) and is wire circuit number 22.
The modification by the Cdn army was to add a single filament light unit on the right side of the Jeep on a separate bracket. The lamp unit was similar to that found on the railroad crossing arms. However, your best bet is to change the BO tail lamp assy for the same assembly that is on the left side. That would mean you would not have a BO brake light, but if you really wanted one you can install a lamp unit similar to your front BO marker but with a BO brake lense.
All these lamp units are available form the various dealers, and are also always on ebay.
Note that these early military lights, along with the later first generation of composite lamps (introduced in the 70s) are not SAE approved, and if your vehicle is subject to a safety inspection, may not pass if the inspector knows his stuff.
The NOS BO headlamps I have are all black. They are a PAR36 sealed beam unit. You can pry open the crimp and get to the glass, and they will recrimp reasonably well.
There are also some large tail lenses available to replace the rear tail lenses. They give much improved visibility for road use.
Re removal of those pesky little screws: Good luck. There was a CFTO on that very subject, and they were to be drilled out and replaced with common self tapping screws. Personally I never had much luck removing them, and with a list price of around $30 for the complete lamp unit, it quite frankly was not worth the time spent extracting them. They are the victim of dissimilar metals. I would suggest some silver loctite antisieze when installing them initially.
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