I wish there was a program or website that had the outlines of countries and a list from which you could select cities and areas to be plotted on the map which you could then print. For example, an outline of Britain and then I could click the boxes for London, Oxford, Cambridge, Sussex, York, etc. and I would get a map with only those places I'm interested in instead of a map with so much stuff that it all ends up being kinda meaningless.
Of course it would also have to be able to show areas from different historical periods.
I'm no computer programmer, but surely in today's marvelous digital world that's not too difficult a task, is it?