So during some more driving this weekend, I checked on the lights several times to see if the wiring or connectors were heating up. I drove with the lights on for varying amounts of time, anywhere from 5 minutes to an hour and a half, almost 100% low beams, and checked each time I stopped.
I noticed no significant heat from the wires or the connectors. The lenses felt a little warm after stopping for a minute with the lights on, but I attribute some of that to infrared radiation and not simply from the bulbs getting hotter than usual.
I was reading some pieces on lighting that suggested the quality bulbs have better insulation between capsule and base, preventing excess heat from reaching the connectors. I'm not sure if this is true but it's an interesting idea. The stock wiring isn't really any lighter than the wiring that comes with the Hella Rallye 4000 lamps I purchased (two 100 watt lamps in the kit with a Hella-made wiring harness.) My gut feeling is that the wiring should hold up fine.