I agree with you K4B, if you look at the total area in Google Earth, it's potentially four times the size of the Donut carpark. That gives a lot of scope for originality, like re-routing the roads to provide a pedestrian friendly link to the town centre. Unfortunately, no matter what is done, I doubt it will make Chesterfield much more of an attractive destination for out-of-towners.
As for the existing empty shops, if they don't cater for current need by virtue of size, location and overheads then they'll remain empty - not a lot can be done about that.