Taking Western Sahara as an example, I’d suggest that any wiki page explaining “why things are as they are” should mention:
- a bit about the history (Spanish withdrawal from Spanish Sahara etc.)
- the various claims
- the occupation of most of the territory by Morocco
- the political opposition to that (Polisario Front and others)
- the building of the “Moroccan Wall” and the fact that that is visible on imagery available to OSM (select Esri to see most clearly).
- the discussion of “how best to represent this area in OSM” that took place on the old OSM Boundaries forum. See also my answer to this help question.
- other oddities like the ISO code etc. See also here for the TLD story (ICANN did not grant the use of that to either competing party).