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I found a nice picture window on the cheap but its frame weeping holes are designed to drain in a horizontal orientation (one in each lower corner).

I have mounted it vertically, so now there is a weeping hole in both a single top and single bottom corner.

I was thinking I might seal the hole in the top, and drill tiny holes in the vinyl at the bottom.

Is this a good idea?

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What kind of window? Single hung? Double hung? Casement? –  The Evil Greebo Oct 17 '12 at 13:31
    
@TheEvilGreebo It's a picture window, I updated the question. –  Matthew Oct 17 '12 at 15:17
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You will certainly need to provide for some drainage of the now "lower" track of the window so that accumulated water can flow out.

One thing to also consider is the overall design of the window itself. Many window units are designed with a definite UP and DOWN side to them. When you rotate such window by 90 degrees certain aspects of the window may be less than optimum for proper operation of the window. In particular with a window designed to be opened you may need to adapt certain aspects such as locks, latches and mechanisms designed to hold the window open. In the worst case a slide for the movable part of the window which was on the side now ends up on the bottom. Accumulated dirt in the track could make the window hard to open. The exterior top edge of some modular windows are also designed with a upper water drip edge which you may now have to substitute with a separate part in the installation.

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I should have noticed in the OP that this is a solid picture window. It doesn't open. –  Matthew Oct 17 '12 at 15:18
    
That is a big benefit to your application!! –  Michael Karas Oct 17 '12 at 16:32
    
How do you recommend I "provide for some drainage?" Drill pin holes? Cut channels? –  Matthew Oct 17 '12 at 17:25
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