I have a 40 yr old ranch house with single pane, double hung wood windows. The glazing on them is shot, they don't stay up by themselves, and in the winter they are very drafty, even with aluminum 3-track storm windows. Obviously it's time to replace the windows. But because of other exterior problems, I had my house sided last year with new vinyl siding (on top of the old wood siding). I don't want to do anything to damage the new siding. I do not like the look of vinyl windows inside my house, I want wood. On the outside vinyl or aluminum is fine. Also, I'd like to get rid of the ugly aluminum 3-track storms/screen attached to the outside of my windows, so I'll need screens as well as windows. I live the Chicago area, so I need windows that are appropriate for that climate. What are my options to replace these windows, without damaging the siding?
Anderson and Pella are the best.
The windows can be done from inside, and unless your sills are rotted out, there should be nothing to do on the outside except some caulking.
With a quality replacement window, any storm/screen combo is unnecessary.
Look for a window with thermal panes (insulated glass) with Low-E.
If you want the wood look on the inside, but don't want the maintenance hassles that go with it, there are all vinyl windows that offer a "wood" interior. The interior is a wood "foil," giving you the wood look without the care of real wood. There are companies out there that do a very good job of this "wood" technique. I have a turn-of-the-century home myself and chose this option in my own home.
I would only caution you against one brand, and that is Pella. I personally feel they use some creative wording to sell slightly less than what really is, and strongly dislike the repairability of their windows.
Brands I like, think offer quality and repairability, and will work in your climate include: Heartland, Anderson, Great Lakes, and Lindsay.