Trevis Martin conventional wisdom usually says Cuba Libre, because the map is small and it’s essential COIN, without any of the widgets that have appeared since then. It’s pretty compact!

If you have experience with wargames, assuming you don’t trip over the lack of hexes and chits, I’d recommend A Distant Plain. It’s still my favorite, mostly because of the subject matter and because the conflicting asymmetrical victory conditions are most delicious.

I’ve played the most of Liberty or Death but it’s the first one to really stretch the counter insurgency model of the engine. It also adds a lot of widgets. But, as an American, the map and the ideas were immediately understandable and that’s a huge help imo. It takes a nontrivial amount of bandwidth to navigate maps covered in foreign terminology.