Hilly,
Neoprene overshoes should keep the wind chill off your feet - not prefect tho' I still get numb toes sometimes.
Good advice from Ed re: your gears.
You could try putting the bike on a turbo trainer to get used to shifting gear etc.
The secret is to not "cross chain" - extreme examples would be large chainring at the front and largest sprocket at the back or small chainring at the front and smallest sprocket at the back.
Although your bike may have 18 gears, (9 at the back and 2 front chainrings)there are not 18 "usable" gears due to crazy chain angles etc. Hope this make sense.
If you really want to know what gear you are in, Shimano make a "flightdeck" computer, which as well as showing speed and cadence, will show you what gear you are in.
I use one on my race bike, and find it very useful.
Only drawback is that they are not the cheapest, and a bit fiddly to fit.
Have fun,
Paul