Next Step for Dirty, Peeling Window Sills?

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Q: I just moved into a great new apartment in the city with charming moldings and great light, the problem is the windows have been painted so many times they are peeling, and the sills themselves are soooo dirty. I can't tell if it is rotting or what. I want to sand and paint, but am afraid I might be opening a Pandora's box. Any suggestions on how to approach this?

Sent by Caleb

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Janel Laban is the Executive Editor of Apartment Therapy and has been working here, at the dreamiest of dream jobs, since March 2006.