Hmm, if it was me I'd make it so that any tags the user created on their account BEFORE the import would end up tagging the entries containing that tag, and then do the "include all tags as text footers to entry content" option too. That would make it so that if there were some tags that would be useful to have as tags as opposed to just context, it would be automatic to have them.
Oh, good thought! And DW has the handy tag renaming, in case anyone wants to adjust their DW tags to match their Tumblr versions before they import. Perhaps a note to that effect, reminding people of the possibility when they go to the import page, would be useful.
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