Over-thinking is one thing, I do that all the time. But some good things can be said for at least thinking. Some things are needs, some are just personal preferences. Those are not always easy to separate.
You and the chickens need to be able to see well enough to do what you need to do in there. If it is a walk-in coop that's with the door closed for you. If it's a reach-in you'll let in a lot of light when that door is open. But still the chickens will need to be ale to see when the door is closed.
In summer a cool breeze hitting them is nice. In winter a cold breeze hitting them is dangerous. There are designs where you can have a ventilation opening at their level during cold weather (Woods Coop Design for example) but for most of us having a window at their roost level in winter in a cold climate is not a good thing. So a window you can open in summer but close in winter might be a good thing. But you still need other ventilation, summer and winter
I don't know how cold it actually gets in Massachusetts. People that live where it gets truly cold and have tried different things say they see a difference in how their chickens handle cold when it gets around -20* F. How the coop is built and the breed of chicken may factor into that. Until they get that cold don't worry about trying to give them a warm place, worry about letting them keep themselves warm with their down coat. That generally means keep them dry, out of a wind, and have enough ventilation so moisture can escape.
My personal preference is for a relatively darker coop, I think it is more soothing. Some people prefer a brightly lit coop. I really don't think the chickens care that much. I have one regular sized window in my 8' x 12' coop and it is on the north side. But I also have openings on all four sides up high under overhang covered with hardware cloth. Those openings let in a fair amount of light Consider those openings as in fascia maybe.. Looks like yours on the front might be more of soffit ventilation, not sure how much light that will let in.
My roosts run north-south. The north end near the window is the most popular spot on them. I think that's because of the window but I'm not sure.
I don't know what the right or best window placement is for you. Maybe there is something in here that can help you decide what to try.