Last year was the first year I considered myself riding year round (with a few days or weeks off sprinkled in). I used to limit myself based on the weather, but thanks to stories and advice from other riders I broke through my self imposed barriers (thanks guys ).

My first advice would be to dress in layers. After a few rides you should be able to determine how many layers are needed and in what kind of weather. Plus you can always peel off layers or open and close opennings as needed.

I work overnights so my lighting for my rides are relatively cheap and effective and was built up overtime (about 3 years). Mars had a kit available at some sporting good stores for about $25 which had a 3.0 tail light and a front light both with multiple modes should help as a starter.
This is my setup currently
LHT:
2 MTE P7's from DealExtreme with flashlight holders
1 Nightrider Cherrybomb on rear bag (flash mode)
1 Mars 3.0 on left strut of rear rack (solid mode)

Exile:
2 Fenix Olights with 2 fishlocblocks
1 PB Superflash Stealth (flash mode)

Hope this helps getting you started.