I wouldn't plan everything around painted wood trim! Go with the wood windows, window trim and doors.. you can always replace the rest of the trim later on!

See what it all looks like and if you're not happy with it, you could try changing the trim color. We have dark brown trim in the master bath and it shows every speck of dust so keep that in mind!

Really think it will look fine mixing the 2 for now.

No question in my mind, shellacked or varnished or stained wood is much the better..Anything over paint...
Stain over the prime ??

Thanks for the advice. I am glad to know I'm not crazy for wanting to push ahead with the oak. I think I am going ahead with the wood windows and doors, but trim the windows in white. The doors already have white trim, so they should probably match. I figure if I choose this route, it will match until I can replace all of the trim in a room at once.

I don't understand why everyone is so obsessed with putting in white windows and doors. They might be timeless, but they are a huge pain to maintain given all the dirt they'd show. And in a historic home, wood really feels like the best choice. Plus if I hate it, I can always paint my wood windows and doors white.