Windows in Cleveland take lake wind, long cold, and condensation that freezes on the stool. Old wood double-hung units and loose storm panels stream on a bitter morning. The water stains the stool, swells the rail, and then ices. A failed newer seal fogs and stays fogged when the gray stretches on. Wind finds the meeting rail on the lake side first. A cold room with a live radiator or vent is often the sash, not the boiler.
Brick openings and plaster returns make a poor fit obvious. An insert set in a punky sill leaves the rot in the wall. Full-frame work is warranted when the stool is mush and needless when the frame is still solid. Plenty of doubles still have ropes that failed years ago and sashes painted shut. Say what the wood feels like. Chalking paint should stay contained, not sanded through a plaster room.
Bedroom windows over a porch roof take the worst wetting, because ice and splash keep the sill wet for weeks. Ask how the opening is flashed and what fills the gap, especially where driven rain comes off the lake. Interior trim and an outside cap belong in the finished job. Hardware can be repaired when the glass is clear and the frame is sound. Forcing a frozen sash cracks it. Count the openings that leak air, not every window on a close-set face.
Summer humidity still fogs the same failed unit the winter only chilled. That does not make this an inland condensation story. The dominant problem is cold driven by a long fetch of wind, and the draft you feel in January is the one to describe. Alley-side and lake-side windows are different exposures on the same house. Narrow lots mean access is part of the work. Say which floor and which face hurts.
Lead with the lake-facing wall if that is the one that ices the stool. Say whether you are fighting a frozen meeting rail, a rotten sill over a porch, or fog in a newer insert. On a double, the draft may be one floor only. Call the number on this page.