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.
'02 Eddy Merckx Fuga, Selle An Atomica
'85 Eddy Merckx Professional, Selle An Atomica
'10 Soma Double Cross DC, Selle An Atomica
Slacker on wheels.