The point of having chocolate milk for recovery is that it has more sugar than regular milk, so the carb / protein ratio is more like 3:1 or 4:1. Obviously, how much you drink and how long your run has been are things to consider as if you've only run 3 miles and then drink a pint of chocolate milk, you'd ingest more calories than you've burned off. But the idea is that after hard / long runs, replacing some sugars quickly will prevent catalysis of muscles. Which brand you use is largely a matter of personal taste / budget / convenience I'd have thought.
I have a lightweight jacket - it doesn't get a lot of wear. It has to be cold as well as wet for me to wear it, as I find it very warm otherwise. I find a cap with a peak the best thing as somehow if the rain isn't hitting my face, it doesn't feel like it's raining so hard!
For me, it's just one of the differences between training and racing - I nearly always train with music, and I've never raced with music. Never missed it either - for my first marathon I had my ipod with me in a pocket but didn't use it as I didn't want to block out the amazing atmosphere that was around me. Even on less well-supported races, there's still a different atmosphere than when you're on your own in a training run.
Sorry to be another person saying "oh, just run without music"... but you surely weren't expecting a chorus of agreement with you on this topic, were you?