Steven Den Beste:

"During the time that I was wargaming heavily (about fifteen years, starting in about 1978) I played many different kinds of games in many different formats, placed in many different eras, some historical and some synthetic, some highly abstract and some very realistic, some even set in the future. I was an avid computer wargamer for a long time.
When you play a single era intensively (like my experience with Napoleonics) you grow to learn the details of that era very well. But when you play a lot of different games, you begin to see certain underlying factors which apply everywhere, under all circumstances."

Good essay on USS Clueless about war and wargaming. The part about chaos rings very true. When I was trained as a reserve officer, I was amazed how the simple infantry combat situations we simulated seemed confusing. A plain ambush in a forest is just a dozen guys waiting hidden behind trees to kill another dozen guys who happen to pass by.
But when you play it, it’s a lot of noise (loud brat-brat-brats from all over the place) and it’s even hard to know where the action is happening. A couple fake grenades pop up, a guy walks on a fake landmine (which releases smoke to signal a hit), and it’s over. You can’t help thinking that in a real battle, you’d be dead or wounded without even knowing what had happened to you. No wonder it takes 1,000 bullets to kill one soldier during war times. Most often you’re just firing at air.