The one thing I need to do is find a better jacket. I have a waterproof Columbia jacket I picked up on clearance-not perfect, but it works. The few days that have seen snow/rain combo at 33-34 F I have thrown on a short sleeve wicking top and 1-2 wool shirts from the thrift store. If somewhat wet and windy, I throw the jacket on despite some of the overheating/sweating issues. The wool does it's job at keeping me warm. I have a cheap fleece zip up (I've had it for a while) and I've been finding it does a decent job for wind.
A day like today, 35-40, I was fine with a pair of wool mittens, wool cap under the helmet, the short sleeve top, wool shirt and thick wool sweater. Also had 2 pairs of nylon track/warm up pants, 2 pairs of icebreaker hiking socks and a pair of sandals. It was just about perfect.