My own experience is that it's rather easy to draw a light map and deal with i18n. There are several open data sources and libraries. The hard problem is purely administrative. If you have data tied to most countries, there's certainly a mismatch with your source for a map, and you have to build a custom map yourself.
There is no consensus on what a country is. A few examples of divergences: Western Sahara is officially a country, but practically it's always been occupied by Morocco. Somalia is a mess, with Somaliland and Puntland being de facto independant coutries though noone acknoledge them officially. Between these two categories, Greenland, Nue and a few others are not fully independant.