I do five miles. I am cold for the first half, then I am warm for the finish. If you aren't cold when you start out, you are overdressed for when you finally build up some heat. I find that when I am cold early on, I slow down instead of speed up. Yes, you generate more heat by picking up the pace, but you also generate more wind chill. A mile from my house is a gentle hill, after climbing it slowly I am usually warmed up, but before the hill I take it easy to reduce wind chill.

For clothing, I use cycling tights and wool socks. I have winter cycling shoes with spd cleats. Up top I use a form fitting inexpensive synthetic base layer from target. Over that goes a terramar base layer, over that goes a wind breaker. My face gets really cold the first half below 30 degrees, I might put on a balaclava. This set up has worked well down to 17 degrees for me, with one exception. My inner thighs get cold near the crotch. Since my commute is 25 minutes at most, this is not a big deal. However, I am going to experiment with something under the tights and something over the tights to try and eliminate this. I could also switch to wicking long johns and a wind stopping layer over that, the trick is not to get too hot and sweat a bunch. I have all sorts of clothing from downhill skiing, XC skiing, and cycling to experiment with.

I don't think you can escape the trial and error process. And each new temperature range will be a new challenge for you, but I bet you will have it figured out soon enough. Strategic layers that you can dial in is the key. You also have a short commute, so any errors you make won't make you miserable for very long.