When I was working on the overnight in DC I didn't have to pay for parking. Now I work during the day and its $12 a day. So Im going to ride during the winter. I've got some decent gloves, I will be bundling up. I need to find a way to prevent the wind from leaking into my helmet. As far as the bike, what should I do to her to prepare for her winter.

 

Move to Florida.

 

I used to live in Maryland. It gets below freezing, frequently.

What do you intend to do about slippery road surfaces? That's way more important, and way more dangerous, than getting cold when you ride.

I think your first and most important decision will be to take the cage when it's below freezing, or projected to be below freezing.

 

Oh man the salt and grit are gonna take a toll on the bike. I understand if you have no choice, but rotors, pads, belt, etc., are going to take a hit. Not even mentioning the finish on the bike. Find a way to wash her with warm water at least weekly.

Cold batterys have less cranking amps. Make sure you battery and charging system are up to snuff. Keep it on a tender overnight always.

Can you fit a thin Balaclava under your helmet? That may help the most.

 

Carhartt Wind proof fleece neck gator is the single warmest piece of gear I own.

Pull it up in my helmet to my chin, keeps the wind off my neck, and from leaking into my jacket.

 

How long of a commute in time and miles? My limit is about 25min over 17miles at 40* at least.

A modular helmet sure helps the face but a belacava with my 3/4 with a face sheild is warmer, easier and I think has better outward visibility. I hate the bulk of winter gloves but my regular summer gloves are only good for about 5min tops.

The Cycle Gear 'Freeze Out' stuff is pretty good and we have a few pieces that layer in real nice as tempeture requires.

 

Take the metro, DC drivers are some of the worst so can't imagine battling both them and the weather at the same time. Godspeed....

 

A really really long and bulky (knit?) scarf, wrapped around the neck several times, keeps the neck warm, and also does a good job of closing the gap at the bottom of a full-coverage helmet.
Tuck the ends securely inside your coat. You don't want the thing coming unwound, and catching in your rear wheel or something.

If the ride is more than an hour, you might need heated gloves.

I've ridden occasionally during Michigan winters, as long as the roads were dry. Dry salt on the roads doesn't seem to hurt anything. I wouldn't take my scoot out in saltwater.

One thing I've noticed is that the oil collects a lot more water. It doesn't get hot enough to vaporize it effectively. If I was to ride in the cold regularly, as you are considering, I might pull the drain plug every once in a while, just long enough to let the water at the bottom drain off. You don't want an ice dam blocking the oil supply from the tank. The Harley manuals actually warn about ice blockage when operating at low temperatures. Harleys don't have a "flow-through" crankcase ventilation system like most cars do, so they accumulate more water.

 

A leather fleece lined bandana pulled up over your chin, then put on your FF helmet keeps the wind out well. Works for me in the 17F weather here.
No snow accumulation yet so I'm still riding. Just watch for the icy spots. Do not lean (turn) on them or use the front brake.
Light back break to test tire grip, then light front brake.

 

Some cold weather riding tips in this photo.