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The designer doesn't need to necessarily be familiar with SD itself but there are a few things they need to be familiar with. I have integrated a lot of designs into SD myself and it can be frustrating if the designer did not create the design with a CMS in mind.
Usually I have the biggest problem with integrating the recent/upcoming update template into the tour and issues with displaying images and having them center on the page without altering the design layout. Especially now that sites tend to have much larger images.
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