I would resurrect Microsoft Streets and Trips. I have never used it, but my father still does, and swears it is better than any online mapping software. Part of the reason I would like to resurrect it is that then I would no longer have to figure out how to install his ancient CD copy of it on whatever netbook he buys every 2-3 years.
Some of the fondest memories I have from childhood involved Microsoft Streets and Tips. Father was a military man, so we were always traveling either for moves, or for some other reason related to his career.
He delegated to me the task of putting together his route using Streets and Tips, a great introduction to navigation, mapping and spatial reasoning. Been a cartography geek (not to mention massive road geek) ever since.
