Weep or Vent Holes in Wood Storm

I have a 4' x 4' 20 pane fixed wood window in my family room. There's a 2 pane wood storm that has been previously caulked around the perimeter. I've had occasional condensation, typically on the outside of the inner window. Sometimes it's bad enough to having running drips, so I've cut out the caulk, and taken the storm down to clean both windows. I've glazed and painted and generally cleaned up both. I plan to re-caulk, as the storm does have some small gaps between it and the frame.
Before I put the storm back up should I drill some weep holes or vent holes?
Thanks
P.S. - I'm in Buffalo, NY.
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Yes. On a 4' window, I'd put four holes. I use a punch and make a half round hole with a 1/4" die, but use whatever tool you have. File, grind, drill would work.
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