I think of windows as the eyes of the house. Replace the same type, no sliders, please.

Very cool house!

It would be great if you could match the 2 flanking windows on the first floor. Well, obviously, you can, but at what cost? I'd just replace with exactly what's there (but double-hung rather than single).

thanks @tatts! what does flanking windows mean?

Very pretty home indeed. I don't care for a slider in the upstairs there. Two double hungs will work fine or perhaps you change over to casements.

Have you removed the windows and found out if they're truly beyond repair?

"Save America’s Windows" is the book I've used:

http://historichomeworks.com/publications/

I would replace with the exact same style that is there now.

Great url thank you @OldHouseGuy

Check out this guy's blog. He is very big on restoring old windows instead of replacing them.

The flanking windows are just the two windows on the sides (the 10-over-one sections) of the larger window in the middle in the 2nd photo.

https://www.andersenwindows.com/ideas-and-inspiration/design-tool/400-series-double-hung-window/?frameColor=Interior%3b+color%3dWhite&hardware=Standard+Lock+and+Keeper%3b+color%3dWhite&hardwareOptions=None%3b+color%3dWhite&grilleStyle=Short+Fractional&frameColorExt=Exterior+Window+Color%3b+color%3dBlack&exteriorTrim=None&exteriorTrimColor=Black&side=Exterior#exterior