Should I paint

I would leave the door frame white to match the window frames

You could add some narrow black shutters on both sides of the door. I would leave it white to match the windows.

I vote for white as well. Rather than shuttering the door, paint the chairs black.

Are you going to paint the porch? It appears brand new and the color of it will gray as it ages. I think it’s that new wood that is out of harmony, but that will change. Leave the trim alone for now and re-think it in a year or two.

I'd paint the trim beige and the rest of the pourch the same. If you painted the black already, leave it. Use weatherized paint in a high gloss

Have you considered a nice stain to bring out the natural look of the wood? You can always bring in seasonal coordinating colors by changing up door decor, chair cushions, plants, etc. In my opinion, stain would provide a ton of personality without being to 'matchy-matchy'. Just a thought! It's a perfectly lovely front entrance, to be sure!

YES! We are staining the cedar a semi transparent from Behr called Chocolate. It’s brown tone vs red toned and looks amazing against the siding. Same under-tone.

Great! if you go for a driftwood kind of color Either white or black will be fine. Good luck.

I also vote for white. Otherwise it would get lost.