The Fenix Shillboy
Join Date: Aug 2007
Location: League City, Texas
Bikes: Raleigh F500 mountain bike and an exceptionally old (mid-60's) Schwinn Collegiate 5-speed.
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Couple of thoughts...
On headlights, my bet is the less expensive you go, the less water resistant you will find the build on the lights. There will likely be exceptions to that (and I have no true supporting research on it), but I'd have to guess that less expensive lights will be less likely to be built with much true water resistance compared to some of the better built (and more expensive) lights. Again, just my guess.
But, with that in mind, if waterproofing or high water resistance is a concern, you might consider a flashlight (or two) for your headlight(s). For my route on headlights, I'm using Fenix L2D flashlights. They might not be suitable to scuba diving depths or prolonged submersion, but they are extremely water resistant to the point of being dunkable. (As described, they are "Waterproof to IPX-8 standards," which loosely means they can be submerged in water to a certain depth for a certain amount of time without harm. Doesn't mean they can necessarily go to any great depth or that they can be submerged indefinitely, but they should certainly handle any rain you'd ever encounter).
On the tail lights, I have both the Planet Bike Super Flash and the Cateye TL-LD1000 (and I use them at the same time). The Cateye TL-LD1000 is built to be water resistant. The Super Flash doesn't necessarily claim waterproofing or water resistance (as far as I know), but there is one thread in the Bike Forums about someone's Super Flash going through the wash unharmed. It did take in some water, but continued to function. However, my bet is that the Cateye TL-LD1000 (or the 1100) has more true water resistance than the Super Flash.
So, there are a couple of extra tidbits for your consideration, for whatever they might be worth...