I think you're right to be concerned about riding in the dark. It requires a lot of focus, in addition to lots of lights and reflectors. You can't let your guard down for a second. The thing that concerns me as much as visibility to traffic, is hidden ruts or rocks in the road. Easy to take a header when you least expect it. That said, it can be a really Zen experience, when it becomes you chasing that beam of light. It's pretty cool.

I use a helmet with an integrated system that has a headlight, and 3 tail lights. I also have a Minewt light for my handlebars, and another red blinky on my seat post. I have reflective strips on all my jackets, and on my tires. The thing I like about the helmet light is that it moves with you, so you're lighting where you're looking. I can then aim the bar light further ahead than I would if that's all I had, which means I can safely ride a little faster.

I don't ever start a ride in the dark, but it might be totally dark by the time I'm done. If I have a mechanical, I'll call for a ride. I'm not going to stand by the side of the road fixing a flat in the dark if there's an alternative. Most of the roads I ride in the dark on are well lit state roads, not winding country roads. It's what I'm comfortable with at this point.