From your description of the problem, my first instinct is to wonder about a crack in the foam liner. This would create the same situation as you theorize where water gets between the foam liner and the fenderwell drain but does not go down the drain line. This might be more likely if the painter removed any portion of the foam liner during the paint job.
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1999 996 C2 - sold - bought back - sold for more
1997 Spec Boxster BSR #254
1979 911 SC
POC Licensed DE/TT Instructor
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