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Start the expansion whenever you feel like it. If you start it after finishing Dorn's Deep, you will have lots of cool magic items to make the expansion easier (although that works the opposite way as well). OTOH, if you get all the rockin' stuff from Dorn's, you may not want some of the items in HOW.
However, it shouldn't really matter, and many people start HOW as soon as they can while others play HOW after they've finished the entirety of IWD. Whichever way you choose, if you decide it's too easy you can increase the difficulty level and get a challenging gaming experience that way.
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Where there is a great deal of free speech, there is always a certain amount of foolish speech. - Winston S. Churchill
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