The Historic District

Cassidy, we’ll that looks nice. For the period I think the windows would have been anything but white, I could be wrong, the period your home was built was the hight of the Craftsman period white was not an option, a earthy colour to compliment the body colour would be the norm. Colonial and the others may have a better understanding of the period.
As far as the aluminum triple tracks, 3/4 of Gothichomes windows have triple tracks and I have been questioning what to do with them for years. They are very functional for getting air movement in the home and do their job well in the winter so immensely practical if not a bit ugly. They can be painted, but need to be scrubbed and etched well, or the paint will not stick.
Your front porch, it looks to be rebuilt?

I definitely see where you're coming from on the white - however, the 1916 Aladdin paint card I was using as a guide for picking colors suggests white, "flesh tint", and "centennial brown" as trim options for the color. I think that while the craftsman aesthetic was the fashionable ideal, there was also a strong strain of colonial revival going on at the same time - they also suggested white as an option for trim with some of the greys, browns, and olive, which might have also been seen as potential revival colors.

Yes, the porch was rebuilt ... I am not sure when. My plan is to paint it next year, mostly white but with some yellow and then grey on the floorboards. It used to really bother me when the house was still dark brown, but somehow the shingles being yellow make the unpainted boards less offensive.

At Fix Farrington, we replaced our old triple-tracks with storms from Allied. They were one of the few options that the Historic Preservation Commission would approve. They made a huge difference in our winter heating bill.