How to paint (very) old window frames without painting them shut
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If these are double hung windows with sash cords (that look like clothes line) you would best remove the window sash itself. Then you can repair and clean the window too. If you don't want to go to that much trouble, remove the stop (the long skinny piece that holds the window in place vertically.) Paint that separately and the window frame will be more accessible.
Paint them with the window slightly opened.
Just be careful as any paint before 1964 will have a lead base.