The problem is that the storm windows are more energy efficient than the windows. Warm moist air is leaking out of the windows, and condensing/freezing on the storms. There are ways to rehab old windows, which is not inexpensive. Or you can replace with architecturally correct windows, also not inexpensive. Most of the things you suggest will help. Reglazing, caulking, weatherstriping, etc, can't hurt, and is not expensive if DIY. Storms definitely need bottom vents(weep holes), which is why they are there, to let out moisture.
Wayne Dalton has a winding mechanism that is fairly easy to use. Instructions should be available on their website, but not much else. For single doors it is on the right side facing the door. You need a power drill with a 3/8 socket. Loosen locking bolts, and unwind to 0. If you get to this point, get back to us.
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It's hard to open your windows. They seem stuck and do not slide up and down easily. You can see
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