Hey thanks for the answer on the flags... my hub rides with one like that and it disappears. He's on a recumbent, making it even worse.
As for rain and visibility, I just received my Solas 40 rear light and man is it bright. So worth it! I have a cateye on the front. Both are usb rechargeable, which is necessary. The batteries for older lights were completely unpredictable. This Solas 40 actually has a light that indicates when you need to recharge the battery. How cool is that?
Also -- the neon yellow jackets are by far the most visible on the road. You can find a wide variety, some with reflective tape. My new one has a velcro attachment for a hood, but did not come with a hood.
There are a lot of ways to cover your head to protect from the wet, and you want to be sure your peripheral vision and your hearing are not impaired. My headgear is a helmet cover with reflective piping. I found that the bacalava wasn't good because it covered my ears, making it harder to sense when car was approaching.
Get ready for rain..this winter is gonna be wild.

Nancy in Seattle