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My fears are that doing both will make Yahoo and other engines suspect something is amiss, do you have any advice on how to do this without threatening the #1 position that the site has for their core business terms?
The reason the site is changing is it needs to convert more sales otherwise it wouldn't be being re-designed.
Site design is another issue completely. My advice would be to migrate the design (new links, pages, etc.) over time. Start by adding a few main topic links within the home pages or well-indexed pages of the current site. As these new pages and links become indexed start 301'ing the old pages to the new.
I would really evaluate taking 6 months to 1 year to make the complete transition if the site is the main core of business and ranking is a must!