For a long time, I've been interested in the COIN (COunter INsurgency) games. They're discussed here.
I may be on the verge of getting one.
All of the games look interesting. Not a one seems wasted.
I gather Cuba Libre is the easiest and most accessible of them, but I watched a (fun) playthrough and I think that's enough for me. The GMT games website recommends it for a starting game, but I won't drop $80 on a game to learn how to play a different game I get.
Out of the remainder, A Distant Plain is fascinating, and topical, as we're in year, what, 20 of the US involvement in Afghanistan? Kids born after 2001 could be serving there as I write this. And the game's approach - that even your allies are not 100% aligned with your goals - is a solid one.
Here is a video look at it from GMT games.
But I keep coming back to Fire in the Lake. It covers the US involvement in Vietnam during 1964-1972. It's an easy game to divide into four factions: the US, ARVN (the South Vietnamese government and forces), the North Vietnamese government, and the Viet Cong. Each goes into two sides with related but not identical goals. What puts the ARVN into a good position isn't always exactly what satisfies US aims in the region. The VC and NV both want to topple the south, but they don't have identical views on who should be in charge and what "reunification" under Communism means.
I'd be playing it solo, almost certainly. If I got, say, Pendragon, I bet I could get three players to join me. Fire in the Lake, maybe, maybe not.
But it's sooooo tempting. I'm much more interested in 20th-21st century insurgencies than in Roman Britain, say.
Here is a review of Fire in the Lake.
I've started poking around to see if someone has a used copy of FITL 2nd edition . . . if so, and it's more in my budget than an $80 new game, I'll get it. Otherwise, I may just have to think about finding a way to play it and splurge on the game new.