sounds like a plan.

You should have leaders even with a short run of roof. Paint them to match the corresponding siding color.

I think your idea of a shed dorrmer is a perfect solution. You can use brackets for support.

I would take the shutters off the two sets of windows. The other windows without shutters look good.

I think would be ok with awning.

I like celery’s rendering and agree with the no shutters comment (the facade appears cluttered).

It’s a handsome home. Very nice. The green color is perfect!

(Is that basketball goal on the street?)

IMO no portico on that house get the drainage issue fixed then add a simple awning , The fornt of the house is already too busy with angles and box outs .Also no shutters