Seems to me it would entail auto-generating a showcase item for each user (at least for the members who have data in their profile) and then importing their user profile fields into the showcase fields for the item. The potential downside to this would be having a bunch of showcase items with no photos. But I have an idea for that too - on our site we ask that our members use a photo of their car as their avatar, so maybe a cover image could be generated from their avatar.
What other issues should I consider? Any advice on how to achieve something like this? I'd be willing to pay someone to write some code, and I can do all the field mapping in the file and any of the non-coding part of the work. I'm sure a lot of members will jump in and create items, but man it would be nice to have a lot of the data in there already right when the site switches over.