Today’s RPGaDay default prompt is “Map” ( there is a ‘roll 1d8/2’ mechanic to get one of four options).

I enjoy the look of maps that look a little dated and hand-drawn, like the famous map of Middle Earth:

They remind me of the medieval T-O maps, which looked like the one below:

Most maps today are used for navigation, so we expect them to be accurate and precise. We’ll navigate to Google Maps in order to know exactly where to travel past, how far that is, and how long it will take for us to get there. We expect it to represent exactly the path we traverse in small. T-O maps, on the other hand, were not maps to navigate by but rather maps to indicate what the world looked like. The east was positioned at the top, because in medieval Christendom, Jerusalem was at the top of the world, and Jerusalem was to the east of Christendom, i.e. Western Europe. Maps, as you can see, can be a political message in and of themselves. (Incidentally, this may be one of the sources of the mistaken belief that “people” used to think the earth was flat—it’s been common knowledge that the earth was a sphere since antiquity).
This is also true for the map most of us will be familiar with, which is one using the Mercator projection. While this is a map used for navigation, this map also distorts the reality of our geography, because we’re trying to fit the surface of a sphere onto a flat rectangle. As a result of the Mercator projection, the surface areas of regions farther away from the equator are distorted to be larger than they are, which creates quite a shocking effect if you look at the difference between actual size and Mercator projection size:

There too, you can see a political message, as in most languages “big” is taken as a synonym for “important” (think, for example, of the expressions “you’re going to make it big!”, “big things are in store for you!”, “big things are about to happen!” and so on). In the case of our geography, you can see how this exaggerates the relative size of Westernized countries as compared to equatorial ones.
Now, what does all this have to do with RPGs? To me, this shows that maps and representations are important to the story you’re trying to tell. The very shape of the map itself will transmit a strong message to players. Have a very detailed map with measurements and a five-foot grid marked in inches on it, and you’re clearly communicating that this will be a miniatures-focused battle map for an encounter, for instance. If you have a map that shows every tiny little detail, then it suggests that each of these things might matter, or might be relevant.
Personally, I love that style of map that the Middle Earth image above shows. It gives some details by letting you know where forests and mountains are, but it keeps things vague as well; where, for instance, does Rohan stop and Mordor begin? We can assume that mountain range, but you can’t exactly be sure. Is the distance between the north and south of the map equal to the east and the west? It doesn’t really matter – just know that the rough shape looks like that. In fact, if you look at where the details and specificity of the map is, combined with the rough shape of the map, you can see what its singular message really is: there is a path from the Shire to Mordor. Without saying that, the map communicates exactly that. Everything around the places relevant to the story are vaguely handwaved to or omitted altogether.
That, to me, is also the best type of map to use for RPGs. The details are not particularly important. It’s similar to J. Michael Straczynski’s comment when asked about the inconsistencies of the travelling capabilities of the starships in Babylon 5: they travel at the speed of plot (the actual quote is quite hard to find, but it’s repeated frequently and has not been debunked as apocryphal). What RPGs bring to the table (sorry-not-sorry for that pun) is an imaginative space to explore interactions in. So, much like a T-O map, I prefer to tell players what the places are that they’re interacting with rather than precisely where they are. A place 13.4km to the north is not as interesting as a place that’s through a dark and twisty wood. A week’s travel away is dull; a week’s slough through a desolate wasteland is a risk. An exact map of a port tells you what it looks like but letting the players know that it’s “a wretched hive of scum and villainy” tells you exactly what to expect.
Any map that you present to players in whatever form isn’t a picture, it’s a collected set of ideas.
You mention maps being political, and that is, of course, true. It made me think: have I ever encountered a scenario or game in which different factions were using different maps to push their own agendas, with the characters caught in the middle trying to infer what the _actual_ layout of the thing is based on these contradictory maps? I don’t think I have, but it could make for a very interesting premise. Hm…
That’s an interesting plot! There’s plenty of examples, of course, of contentious maps, like the status of the Western Sahara (I believe there are currently give different views of who it belongs to), but that’s more a question of ownership rather than existence.
It would be fascinating to write a module where the players engage with a group of subaltern status (or are themselves part of it) and the various hegemonies trying to wrest control from each other. I could imagine a scenario where there is a supposed treasure being sought after by various factions, each with their own myths of where it would be, each with only part of the truth as myths will always distort reality in some way.
A party could get embroiled in this because they’re just trying to move from A to B to reach their family member’s wedding party or somesuch thing, and they’re barred from passage by faction A, B, and C, each claiming different laws and regulations and so on.
Hrmm, might be fun to write something like this up for sure.
Or the ‘abandoned ruins’ marked on the map turn out to be sacred ceremonial sites of the indigenous population (to just run with the colonial themes of D&D and make ’em really blatant). Or a situation like Northern Ireland, where part of the population believes they should be part of one country and the other part believes they should be part of another. Characters acting as bodyguards to a tax collector or smugglers (perhaps at the same time!) get caught in the middle…
I was also thinking of the possibility of the map being a blueprint of a house or manor where the players are looking for something but the house has been burnt down and rebuilt two or three times so none of the maps corrently represent the space.