When I first bought a dynohub (back in 2013) I picked up a couple discontinued D Lumotec Oval lights on a clearance price. I ran the two headlights wired in series, I needed to go faster to get the lights to initially light up (instead of a rapid walk pace, I needed a jogging pace for the lights to light up) but I had twice the light at normal riding speed.

Thus, I think it should work fine for you as long as you do not have to pedal slowly up a steep hill that is tall enough to take more time than your standlight will last, as your standlight might be your only light at slow hill climbing speeds.

Taillight, I did not use a dyno powered one but since taillights take very little power compared to headlight, I would assume it would work but like the headlight it might not work well at lower speeds.

I think you need to wire in series, but wiring it in series means that both lights have to be turned on, as each electron will go through both lights, turning one light off would turn both off. I have no clue if it would work in parallel, I only tried it in series.

Since then I have bought better lights and went back to a single headlight. No longer using dual lights.