Summer gloves & wool isn't going to cut it as it gets colder. I find a top wind-proof layer to be essential (also good for 10 deg of warmth once I get going) for head, hands, feet, and core. Legs seem to take care of themselves - leg warmers (even the cheap set Nashbar & Performance sells) get me down to approx 30-32 deg. Gloves have been the hardest thing for me to settle on (I now have amassed quite a collection!).

Lights - I like one on bars and one on helmet. Provides back-up and aimability at moving shadows (dog? deer? ninja jogger or rider?) and drivers, especially those coming into the roadway from a side street, driveway, or parking lot. I am a Dinotte fanboy and have purchased several of their lights.

Ortleibs are very nice but are overkill IMO for commuting and especially on a budget. I pack my clothes in large ziplocks as the rain cover for my bags (Axiom) doesn't always work. I used to use a set of Performance/Nashbar panniers; didn't like the retention mechanism. Check craigslist and ebay for someone getting rid of a lightly used set, or even start with a backpack (sweaty back is less of a problem this time of year).

Check places like Target, etc. for off-brand/house-brand base layers and fleece; I've had very good results with Target's "Champions" line as a base layer.