Your Skylarks drain holes were added by some enterprising "driveway engineer." The factory had NONE, and it really works out OK. If your window is sealed properly it will not leak. The problem is, it will rust over time when water is allowed to sit in there. I have seen guys who would blow out the water with compressed air before they put it in the garage.
I have put drains in them before that worked out nice. I drilled a hole in the bottom corner of the channel. Then took a piece of eighth inch brake line with the cut from the end so it had the flare on it. The tube was slipped into the hole from the top so the flare held it from falling through. I then tack welded it in and primed and sealed like the rest of the seams with urethane seam sealer. On the end of the tube in the trunk I put a piece of rubber vacuum hose and ran it out a hole in the bottom of the quarter panel bottoms. This worked very well. The car looked like it was going pee every time after getting wet though.
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Life long Buick fan,
1965 Gran Sport Conv.
1965 Skylark H/T
1948 Chevy P.U. with 401 in it.
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