Many arts and crafts homes were "updated" in the twenties by painting the dark oak trim and lightening the look. Spent way too much time stripping it back off. But you can paint the style and it will look good... Except for the window to trim change. Paint the vinyl? I've actually never seen an "oak" vinyl window. Most have been white, inside and out. A good acrylic paint will bond to the vinyl if you decide to make that change. It would be cheaper tan buying oak and painting it for trim.

Thanks for the reply, I almost forgot that I posted the question. As for the windows, I have never seen any others like them. I think I can get away with just painting the wood trim around the windows.