Some pictures would help. I am not sure why the roof would have an effect on the windows?

no overhang

you're fast!

I'd hate to see vinyl replacement windows in this house, probably some sort of wood window with a clad exterior which would not be inexpensive.

The ultimate window for this house would be something like Hope's steel windows, but unfortunately those are very expensive.

These are Marvin Clad exterior casement windows, which stylistically would be very appropriate:

Thanks very much! I agree, wood with metal clad exterior would be great. Unfortunately I live in a small mountain town so manufacturing and installing are decoupled. I need to find a local installer who "gets it."

Cheers!

I am not sure I understand what you mean? I grew up in a town 90 minutes from any sizeable town and three hours from the nearest city (the adjacent county has about 5000 pop., no four lane roads and no mechanized stoplight), but people who built or remodeled houses were still able to get nationally manufactured windows and someone who knew how to install them? I am not trying to be argumentative, I just am not sure what you mean? Marvin, Pella, Weather Shield or companies like that would probably be able to direct you to the closest dealer and the dealer should be able to direct you to a competent installer.