Are you sure that it's the size of the holes that is causing the problem? Where does the water go after it passes through the track?
Thanks XSleeper for the quick response! So just to confirm, this is what I'll plan to do: 1. Carefully remove the stops and leave the rest of the casing (that the stops are currently stapled to, which are hidden in the picture) in place. 2. Remove the existing sashes, sash guides, parting beads, etc. and dispose of them. 3. Pop in the new vinyl window unit and screw it in. 4. Re-staple/nail the stops back into the casing, and put the trim back on. Does this all sound correct? Also, I'm considering putting in an interior stool and apron, since I already have to rip out all of the trim. If so I think I would discard the existing inside stop pieces, and the new stool and trim pieces would extend an extra ~1/2 to butt up against the existing wooden window casing. Then I'd add new inside stops - a smaller type like a quarter round - and re-trim with an apron etc. Does this plan make sense? Thanks again for your help!
Sounds okay except I'm unsure of how in #1 you can leave any casing on.... seems like you have to remove ALL the casing then the jamb extension... just to get to the stapled stop. but maybe I'm missing something i can't see.
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