What is behind the small window that is beside your front door? Filling in the cut out and putting a front door beside the big window would be easiest if you can do without the small window. Is that the kitchen? Could a skylight bring light into that area if you put your foyer on the porch right in front of it. If that's where the sink is, could you stand not to look out a window while there?

I don't think your "cut out" dates the house; I think your mismatched window and shutters do. I would put in new much bigger windows all of the same size and get rid of the shutters.

Yes, the small window is where the kitchen sink is.....not sure how I feel about losing that window. I do like the idea of having the front door actually on the front of the house though. Thanks for the suggestion!

I would simply wrap the wrought iron post in wood and paint it white. Then you can add a pretty hanging basket from it. Then add a

ceramic garden stool next to your bench, along with 2 outdoor pillows. Ideally, I would suggest you remove all the shutters but at the very least, remove the shutters on the two largest windows.

https://www.target.com/p/canton-stripe-outdoor-throw-pillow-orange-threshold-8482/-/A-78138956

https://www.overstock.com/Home-Garden/International-Caravan-Drum-Ceramic-Garden-Stool/11104424/product.html?option=17139156

Do a trial run by hanging something over that window for a week and see how you feel about it. Is it the neighbor's house you miss seeing or just the light? Maybe a skylight could do the trick.

Removed shutters from front window

Remodeled gable to create porch.

Frankly for what it will cost,...........and you realize your roof shingles will never match unless you reroof the house............I'm not sure it's worth the expense.

You could create a semi-circular patio in front to act as a porch. It would add interest to your home and cost far less money.