What goals (interior, exterior) are you aiming for in your renovation? Do you have a budget range?

We have enough space inside to work with, but we are hoping to gain a window or two in the upstairs rooms, to the right and left of the existing dormer. Budget is flexible depending on what end goal we can achieve from this. Ranging from about 30k-80k.

I like the house as is. It's attractive and cottagey. You risk screwing up the proportions if you redo the roof. I'd put in skylights.

That said, if you want to do something major, talk to an architect and pay for bluepprints. Choose someone who does sympathetic renos, not just someone who will do what you want with no regard to looks.

Your architect can sketch windows on a front-on photo of the house. A contractor can make a mock up of new windows with a few story poles on the roof so you can see how the proportions would work. I would use the same style window as you have now.

I need to see the drawings for the new additionor a floor plan of the upper floor to see where you culd add windows without ruining that reall nice looking house If thre is no gain in actual space with what you are planning I would save the money.