What is behind the middle window?

It is a bedroom so it needs an egress

The house is asymmetrical all over. I am not sure that spending in the tens of thousands of dollars to configure something on the inside,move the window a couple feet to the left, and redo the mansard roof just to achieve three evenly spaced windows across the top story is that important. The most obvious place for the middle window to be placed would be aligned over the front door, and that still would not be centered between the two others and who knows how it would fit with the interior plan.

I think one thing you could do is make the steps and entry to the porch wider and less obviously centered on the door. That may alleviate some issues.

Would you prefer all three windows on the top floor are symmetric? If so, check to see which walls are load-bearing. If none of the closets have load bearing walls, make a new plan with new closets to match the new window locations. If it's always bugged you, this is your chance to fix it.

On the bigger situation: Sometimes one item is really all that needs fixing. Sometimes there's one item that signals that there are a whole bunch of problems. Sometimes the one item draws attention away from bigger problems. Sometimes decision fatigue causes questioning of previous decisions. If any of these situations seem like that might be going on, you may want to hire an architect for a consultation.

I don't want to bring you down because you've already suffered a tragedy. But your rebuild is shaping up to be another tragedy. Seems like it's a little late to be changing anything, but you could really use an architect. You had/have an opportunity to fix these things, but if the windows are in already it seems like that ship sailed. I definitely wouldn't replicate the original style of the second story as that isn't done anymore and I think you already know it doesn't look good. You need an architect who can draw up a new facade such that a builder can do it. Builders only build according to plans and usually lack any artistic sensibility. TBH the windows on the second floor in the front look terrible regardless of their placement on the facade - how do they open? Why aren't they double hung like the ones on the back? You have my sympathy - you probably just want to get back in your house.

Thank you for input yes the whole house is asymmetrical - it was a small house and they just kept adding more and more additions to maximize living space instead of visual appeal unfortunately - unfortunately the closet is where the air handler for central air is housed for second floor vents. I’m trying to not do anything DRASTIC to outdoor appearance because of money costs and possible issues with the town. Obviously siding and roof have to be all redone but figuring out what would help the appearance of removing the slanted roof shingles from front and just doing siding - maybe putting some sort of design or something to fill the empty VOID space.

Kandrewspa - they are crank out stupid egress windows the insurance company needs everything to be up to code and I opted to putting them on front because the front porch was what saved our lives we had to exit through the second story windows to get safely out of the house because the fire started on the first floor and blocked the stairs - I hate the look of them but at this point anything to just get the stupid project over with. It’s been almost a year and with delays on material and every thing else.

What do you mean by "slant shingle" and "slanted roof shingles"? Do you mean the mansard style roof?

Apple_pie_order - yes thank you that is the name of the roof style as you can tell I am a newbie with construction terms. I have learned a lot every day through this process thank you for teaching me the correct term.

Here is the back, patched and painted

You have a psuedo-dutch colonial. But it looks like the way it was constructed is as if there is a plumb vertical exterior wall which is what the roof bears on, and this upstairs vertical wall is in-line with the 1st floor wall (at least in back, probably in front but can't tell with the porch). Then the psuedo-look "slanted" roof was added on outside of this vertical bearing wall. If so, that would lend well to just removing this psuedo- shingled "slant" wall to expose the plumb vertical wall.

However, it would be a lot of work and money, as you have to then sheathe the exposed wall, extend a soffit of some sort, and in front probably deal with a porch roof that may fall short of this wall. It would be out-of-pocket, not insurance money.

You also have a nice E30.

3onthetree - thank you for the amazing advice - I just want it fixed correctly because the poor design is causing me headaches and I rather do a design suitable to last another 2 or 3 generations especially with the last blizzard we had it was shooting snow up above - which when it started to melt it began leaking behind the walls in my freshly sheetrocked home. Thank you so much - one of my favorites out of my fleet. The e30 will get fully redone once my project home is completed and I can shift focus back onto my hobbies🤣

You look like upper NorthEast location. RIP BavAuto.

Good luck with the rest of the remediation reno.

Your house is actually balanced in two parts which is how vernacular two bay houses turned into 3 bay houses often historically were.

Thomas Dane House - Concord MA (1657) - although this one probably went 3-bay, 5-bay, 6-bay, and each part it more or less balanced with itself but varies by part over the entire facade.

It seems to me you can look at it like @palimpsest did, as balanced, but not symmetrical or you can fuss over the lack of symmetry. I think it's a nice house. I'm not a fan of asphalt roofing on the side of a house. Plenty of houses in that style in my area once had decorative slate tiles in a pattern in the upper siding/lower roof area, which was attractive but pretty awful when replaced with run-of-the-mill asphalt roofing. I'd replace it with wooden shingles.

You could highlight the architecture by adding steps in front of the single and move the existing steps over to center on the double section — two entrances. Or side entrance(s) and extend the railing across the whole length. It is a long porch. You might want to look at scalloped or more decorative shingles, but palimpsest would know the correct style.