My neighbor has a 100 year old house with big pitcher windows and he has double pain windows installed on the outside as if they were storm windows, they look great and work great, not sure if they have drains on the bottom or not.
moisture drainage is an issue, I would have the drains open to the outside, that way any fresh air that gets in there will be dryer in those seasons when water could condense and the warm humid air from inside the house never gets in that space, to that point you also want to make sure that the windows are sealed well from warm humid air from the inside, making sure that the trim around the window is even caulked tight, everything is painted well and that the sill is not rotting.
Other option that might work is a tiny solid state dehumidifier in each space, you can buy a whole unit for $40 or buy the parts for about $15.
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