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Jakopanda, if it’s any comfort, I think prospective buyers will (for better or for worse) probably be paying less attention to the windows than you think.
I didn’t really pay attention to the style of the windows in my house when I bought it. (Mainly, I noticed that they were new, and was relieved since I didn’t want to mess with drafty windows and replacing them.)
It was only later that I realized that the colonial style nine-over-nine was neither 1) in keeping with the rest of the block or 2) historically accurate. I would’ve preferred simple double-hung, but it’s not a big enough issue to be a dealbreaker for a house, or a big enough deal that I’d even think about replacing the existing windows.
I think when possible, you should try to go for option 1 (matching most of the block) or 2 (historical accuracy). If you can get both, fantastic. And if you can achieve 1 and/or 2 in a “green” way, so much the better.
I’d try to get something unobtrusive and inconspicuous, and relatively generic (even though that word usually has a negative connotation). The more individual and “funky” a window type is, the higher the risk that some buyers will love it but other buyers will hate it.
To my mind, the prairie-style windows are more “funky” than colonial grill-style or simple double-hung. So if you’re choosing between prairie and colonial, I’d recommend going with colonial.