IO::All does a lot of this already. Not the wizard part so much as the almost mind-reading part.
As for the wizard part, I don't know so much about the popup part, but I would think that DBM::Deep would be useful in keeping track of what's happened in the past.
My criteria for good software:
- Does it work?
- Can someone else come in, make a change, and be reasonably certain no bugs were introduced?