You don’t need to replace the baseboard and shouldn’t paint it.

When removing baseboard, there are ways to preserve the old pieces(mark on the back) and reuse them. In your case, I would try to do that instead of replacing with new.

Reason(s)?

Expense. Much less expensive.

Color match. It will be difficult to match the aged patina with new base material.

Labor. Much less expensive to simply reinstall fitted pieces.

Decor. Painting new will throw off the decor.

I would only paint the trim between Door and sidelight. To the someone that mentioned it was time to paint, let them volunteer to pay for paint and paint.

I love your warm stained doors and woodwork and I would never paint them. They also look to be in great condition. My doors and trim in my home are done just like yours , stain color and all. It is one of the best features of my home, I think. My front door stained trim is also done just exactly like yours and it looks fine with a large wreath placed on the door. It draws the eye off everything else. The wreath co-ordinates nice with the wood trim. . Once you paint stained wood work there is no going back. Unless you want to rip it all out. Crate and Barrel has some nice wreaths that would look great on your door, in particular their Red Berry Wreath would look nice .

What strikes me is that your beautiful woodwork is underserved by the yellow tones of the paint pallette and earthy flooring tones. Basically too much yellow is giving a monochromatic feeling. Even those old light bulb colors need to go. Too much effort to blend has instead resulted in blah. Leave the wood alone. Go the other way.