Looking down the road: attack queenside or kingside?

From an 1100-1200 level player, so, not a beginner but make lots of mistakes.

It is not clear to me, during opening play, how to decide whether to attack kingside or queenside. What are the main considerations for this?? I realize that this is sort of "built in" to some openings, but I often arrive at a developed position and find myself musing "What now?"

I assume this should be part of one's thinking during opening play, but it is not always obvious  in which direction one should be developing when one is positioning pieces during development...

Often times, it depends on the type of position.  One cannot just pre-plan one side or the other.  For example, King's Indian players tend to think that it's all a Kingside attack for Black, and in the Classical Mar Del Plata, it is, but in the Four Pawns Attack or the Saemisch, you are going to get killed trying to advance on the Kingside.

Sometimes it's not either side and rather an attack down the middle.  The following are factors you should consider when figuring out Kingside vs Queenside:

Blocked positions are the easiest to figure out (i.e. Classical King's Indian, Advance French).  When the center is BLOCKED (not just closed, not QGD positions), meaning positions that arise from the Mar Del Plata or French Advance or Winawer, you should always attack on the side in which the pawns point, even if that is the side of your own king.  For example, after 1.e4 e6 2.d4 d5 3.e5 c5 4.c3 Nc6 5.Nf3 Qb6 6.a3 c4 7.Nbd2 Na5 8.Be2 etc where eventually White castles Kingside and Black Queenside, doesn't matter, look at the pawns in the center.  White should attack Kingside, trying to force ...h6 and then ...g6 by Black to weaken f6 by maneuvering his Knight, for example.  Black should attack Queenside.  In the King's Indian Mar Del Plata, Black will attack Kingside and White Queenside.

For not-so-obvious cases like that, the things to look for are which side of the board do you have a space advantage, and which side of the board do you have what is called a "Local Piece Superiority".  I highly recommend you go through the following article, which shows a prime example of this concept.  Notice when you look at this article how Black was unable to get his pieces to the Kingside due to the lack of space, and how easily White attacks Black on that side of the board, and wins in a mere 29 moves!

http://charlottechesscenter.blogspot.com/2018/02/game-analysis-lesson-on-strategy.html

If that article was helpful, that was published in February 2018.  I write about 30 to 35 articles a year, starting in June 2017.  I suggest you take a look at some of the others.  There's stuff on Openings (granted, a lot of French stuff, but there are others too), Middlegames, Endgames, and general game analysis, and it's written by an Expert intended for audiences of 1000 to 2000 rather than a lot of those GM books written for 2000 to 2500 audiences.  Give it a look.

Will set aside some time to go through your answer carefully--thanks!!

That is generally good advice. However, I have often been analysing my positions before my opponent plays, so that I often know what I am going to play because he (so far only 'he') has made one of the moves that I analyzed. That being said, wow, it is very kind of you to actually look at my games, didn't expect that! A bit embarassing too, as I have made up to 7 blunders in a single game (though I am getting better and just crossed into 1200 territory...) In my defense, though, sometimes moves that the chess.com computer says were blunders or inaccurate were good moves given the level of my opponent.

The OP asks a very good seldom asked question. While there are specific indicators as mentioned in the thread, I believe the question itself is one that continually needs to be asked from game to game. Greater experience will often obviate the need to consciously ask and seek an answer- just like riding a bike.

The concentration of ones' own forces will often suggest where the hammer bow falls. Sometimes ,like a boxer, the attacker may switch play to the other flank after wrong footing his opponent. (Nimzowitsch called this maneuvering against weaknesses.) Essentially one seeks to maximise one's own mobility while restricting the opponent's.

A good player should be aware of the whole board. When much younger I always used to try and attack on the kingside irrespective of other conditions. This is a mistake. The play needs to understand the demand of the position. Of course, with a more fluid centre, the centre itself should usually be the "theatre of war". (The Art Of The Middle Game - Keres/Kotov comes to mind)

Let’s take a look at when it makes sense to castle opposite sides and when it doesn't.

You should castle on the opposite side when at least one of the following factors is true:

1. When you are up in development and your opponent has already castled, you should consider castling in the opposite side. That way you will have a clear game plan and will also be able to capitalize on your development advantage.
2. When you have a damaged pawn structure (doubled paws, missing pawns, far advanced pawns, etc.) on one of the sides you should consider castling on the other side.
3. When opponent’s pieces are especially active on one side of the board, it is usually best to castle on the opposite side.
4. If you want to complicate the game you may consider this option. That may be true if you must play for a win due to a tournament situation, when the draw is not enough. Also that maybe done when you're playing against a stronger opponent, who is much better in simple/technical positions. That maybe your best bet.

You should not castle on the opposite sides when at least one of the following factors in true:

1. When you are behind in development and you need extra time to develop your pieces, it is usually not a good idea to give your opponent a straight forward way of launching an attack.
2. When the opponent’s pawns are advanced towards the side you’re about to castle, it is not a good idea to castle there (especially if the opponent’s king is castled on the opposite side). It will just give him a positional edge in the attack.
3. When there are open/semi-open files in-front of the side you’re about to castle, you should probably reconsider your decision to castle there (especially if your opponent has castled on the other side). That will give him more attacking possibilities, such as rook lifts, various sacrifices, doubling of pieces on the file, etc.
4. If you playing against a weaker opponent you may want to avoid castling opposite sides, in order to avoid sharp game and keep everything under control.

Note: These are general rules, not laws, meaning that there are always exceptions to them. When you’re making a decision what side to castle you should always take your time and evaluate all “pros” and “cons” and base your decision upon your own analysis. This is a very important decision. It pretty much dictates which way the game will continue. Take your time and think twice.

Fig, white playing on king side, black playing on queenside.

Unstable centre but white has advantage on king side, so white play on king side and black play on queenside (open "c" file)

There could be more than 20 centre pawn patterns,

As a general rule play on the side where your pawn structure dictate!

What side is your opponent’s king on? Attack that side.

I’m kidding, I’m kidding. But seriously, there is a lot of helpful advice in this thread, including the link ThrillerFan provided (good read!). Thanks to all for such high-quality advice.

Indeed. I used to ask this very question to myself back in the day! Cool. With all the various advice given, not much I could possibly add other than some personal opinions based on my own experience. For me, I was always/and am, an openings guy-a book player-who then built the rest of my skillset over the years around certain circumstances (endgame strategy, middlegame themes: positionally & tactically, mating patterns, combos etc etc) as was necessitated. Level of play between my and opponent also developed as yeah, I played the board most often, but sometimes "read" my opponent's play akin to a poker player and made moves to disrupt and intimidate them.

Anyways, as it pertains to your question: queenside or kingside? I believe generally Kingside is always first consideration in any opening from White's perspective because you have the initiative. But from Black's side your first priority is to just equalize. In a way, it's easier to see (on defense) where white may overextend on either side and capitalize later. As it is, if and when the game has approximately equalized (barring an out n out winning attack mainly on the Kside or lost of uncompensated material) weak pawns & squares, what pieces you have and their mobility, outposts, lines that you control, static or fluid islands, open or blocked center will ultimately determine where play will be in my opinion.