I used the Luxos U during the Shenandoah 1200 and Gold Rush 1200. In both cases I had monsoon conditions part of the way. I'd prepared for it beforehand, with the USB port facing the rear of the bike behind my little top-tube bag but also encased in the end of a plastic bag with the cords (USB included) sealed as much as possible with electrical tape.
I keep my Garmin 705 constantly charged and the backlight on 24x7. The only time that I ran into issues was when I stopped on a very steep grade on the Shen and left the light on until it shut down, discharging the onboard battery. I also ran the 705 with the backlight but not charging, therefore discharging it just a little bit.
Oh -- I also have a wired tail-light.
Once the internal battery was discharged, I found that I had to cycle at 12 mph or faster to turn on the USB charger. Clearly, based on my experience, the 705 draws more amps when it's not fully charged. At 5-6mph (this was a very steep grade), the light would flicker like a strobe. This was when the internal battery was discharged.
On the GRR, if I had to stop, I turned off the light, therefore not discharging the battery and never running the 705 even part-way down other than for a few minutes. The only time on the entire ride the 705 lost external power was on the Janesville Grade.
I also found that the electronics in the light will first turn off the tail-light and then the USB charger, in that order. That's ok if you have a wired tail-light with built-in stand-light. I also use a battery operated light so I was never without something showing from the rear.
Perhaps I've been lucky and have not been affected by the rain. The USB is always connected, but with that bit of plastic bag. I did not bother with the connector covers at the back of the light; don't know if that makes any difference plus or minus. I have not done any other waterproofing.
Dave.