Brakes
With rim brakes, either cantis or v-brakes are very good. Cantis are a bit more finnicky to adjust properly so they are easy to apply, but once they are set properly, they are great. But the most important item is brake pads. Right now, Kool Stop Salmon pads seem the best all-weather pads. They perform well in rain or snow and have a good reputation for being fairly gentle on the rim.
Lights
No question that you need them. A generator-based system, especially based on a good generator or dynohub and a headlight that has built-in overvoltage protection, has its merits. Light is well directed on the road (all 3 W or 6 W of it, so 3 W is actually as effective as a 10 W MR-11 spotlight), no need to think about recharging, and batteries never die.
Autonomy is a limitation of all battery systems, and it is even a problem in Winter. I find one of the nicest benefits of a dynohub is that I can ride without worrying about having an empty battery in the middle of nowhere.