I don't wear prescription glasses so I don't wear glasses when riding in the rain so I'll leave that to those in the know.
Regarding 3-5
Here is my clothing list from another thread just yesterday, probably the same w eather system you encountered:
Showers Pass Jacket, Gore Tex rain pants, Showers Pass rain hood, Showers Pass shoe covers, Gore tex mitten covers over Polar Tec gloves. I was dry as a bone when I arrived 10 miles later.
That said, I do sometimes have to dry stuff or I need dry clothes when I get to work. I keep an emergency supply of clothes at work, which includes: socks, another pair of gloves, undershirts, and a regular pair of pants (my work attire is casual but I do have "nice clothes" I leave at work all the time so, if need be I could change into those)
Toughest things to keep dry are hands and feet. The gore tex shoe covers work really well and the gore tex mitten liners are good for about 20 minutes and then the hands start to get wet- I think because they are gripping the bars, which causes some absorption of the moisture on the bars.
Having a set of gloves at work for the ride home and then trading them with a dry pair the next day helps but I've been thinking of getting one of these:
http://www.google.com/products/catal...ed=0CGMQ8gIwAA