Strategy & Tactics
To be honest, strategy and tactics in the real world means one thing. In a game sense, it means something entirely different. I've read lots of books talking about real-world tactics and strategies, but all of them are deeply rooted in the technology, concepts and theories of the day. Not that these are worthless - the exact opposite. But one alone won't tell you how to win a war (or wargame). After reading a bunch of them though, you'll start to see the themes.
This may not sound like a good analogy, but consider card games.
If you've played hearts, spades and bridge you'll get this right away. If you haven't, trust me.
Hearts is a simple game. You deal out all the cards. Then you go around playing cards one at a time in "tricks". The point is to either (1) receive no hearts (2) take all the hearts or (3) prevent someone else from taking all the hearts. Fairly basic, but the key is that there are not many strategic points to remember. You don't have to count cards, but eventually you start to see the game as a whole. There comes a time where you can take just about any hand and try any of the 3 strategies and be somewhat successful - you can see how it will play out.
Spades is similar in alot of ways, but the point breakdowns are more complex as are the rules of play. In addition, there is a "trump" suit that changes the mix. You can't just know what high cards are out in each suit, you have to also keep track of all spades and how many of each suit each player has (because someone may be holding a bunch of spades and no clubs, etc.). Again, play long enough and it becomes second nature.
The point is, you understand the rules and variables after a few games but it takes a while before you can start predicting how the entire hand will go. Experienced players in spades can often do just the first few tricks and then tell you almost exactly how the hand will finish.
Bridge is sort-of the next level up. Instead of playing to take as many tricks as you can (like in spades) you are bidding on exactly how many you can take, as well as what you want the trump suit to be, etc. The game at that point for the good players becomes the initial bidding part. The actual laying out of cards is almost a formality in alot of instances - you know how things will be played (or should be played).
Again, you understand the rules and parameters involved. The machinations become almost mundane. The discovery process of the opponents strengths and weaknesses (as well as your partner's strengths and weaknesses) is where the true game is and where it is won or lost.
I find the same theory holds true for me in wargames. The first game in a system (or returning to an old system) and I'm rusty as heck. It could be Warhammer, CarWars, Battletech, Bloodbowl, whatever. None of the real world advice on how to win a war is practical at that point in time because, usually, the forces are balanced. I can't go off and poison someone's water supply, give them all the plague or spread rumors about them and have any impact on the wargame at hand. Instead, it becomes a matter of knowing enough about the system, seeing how things play out and judging the overall strengths and weaknesses units / models in play. You form a basic plan and then have to continually think ahead and revise based on changes on the battlefield. Still, you're working with a limited set of variables (even though it might be large) so you may find yourself thinking just about the "big ones" (like tracking face cards and aces in any card game). You don't have to count or keep notes, but you should after a while get good at keeping track of the threat(s) each enemy presents and their relative ability to exploit your weaknesses and target your units versus your ability to exploit and target theirs.
At least, that's how I do it. Those of us in my gaming group that tend to win alot of the wargames/strategy games do the same things. We're not all history majors, or are we military buffs in general (although parts of us are for sure). The key is learning the system in which you work and being able to rapidly sort (and re-sort) strengths and weaknesses while you play.
In a fantasy setting as well, planning a war really comes down to a few different levels. First, what can you do within the environment to destory your opponent without a war? (Insert Sun Tzu or other folks here, making sure to take into account the affects of magic, etc.). Chances are most games/DMs don't keep track of the minutia of factors that go into real life - sanitation, economy, food supplies, morale of the city, social class anxiety, etc. Second, once the war starts, what can you do to destroy your enemy without fighting him? Delaying, attrition, spreading dissent, treachery, etc. Third, once you do have to fight him, you don't want to be weaker. If you each have the same magic/tech levels you want to be in a stronger position, more fortified and have more and stronger people. Really, you want this. Finally, once the battle does happen this is when you have to be able to put your strengths vs their weaknesses, protect your own and exploit any breaks you can see dynamically.
On a lighter note, I'm doing a second pass of my mass combat stuff w/ the Natural 20 press folks. It's a miniatures-battle extension of D20, no pretenses about "running kingdoms" or "deciding who wins wars considering factors like supply, attrition, etc."