For me it has to be Rowan's Mig Alley (released in 1998 I believe).
It has pretty realistic flight models, good AI, but most of all it puts you "right there". It has some of the best AI radio communications I've ever seen in a sim (next to Falcon 4) and the campaign is simply a gem: it's really a strategy game inside a flight sim. And then there are those little details: if you destroy enough trucks the enemy will be using mule convoys, or if you destroy their depots they will start hiding supplies in the woods.
On the downside it is plagued by some serious bugs that were never fixed, and the software itself is also rather unstable. In fact I've put the game aside many times in frustration because of this, but I always find myself coming back. And still play it today...
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