on 4th gens...
I know the back corner of the window where it meets the t-top/roof can be a good place, and that sounds like its where its coming in for you. It will get inside the window, follow the sill the whole way down, then fill up the carpet. typically it won't usually drip it will just run.
A window + t-top adjustment may work well for you...also, putting some vaseline on the weatherstripping can make it swell back up if its flattened out a bit over time and it will also condition the rubber.
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87 iroc with the usual go fast stuff
heavier than your half ton.
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