Castling Opposite Sides

I realize this may be a 'depends' type question/answer, but in general, is it better to TRY to castle the opposite side that your opponent castled on, so you can get a good attack going against his king? or does it in general not matter?  or does it mostly depend on board conditions?  

I don't think I can answer that without using the word "depends".

First of all, it depends on your style of play. Are you an aggressive player who cares little about your own defense and is all about attack and sacrifices (like Lasker and Tal [and my friend, even though he's not a grandmaster])? If so, I think castling opposite sides is good for you.

Second of all, it also depends on the nature of the position and in turn the distribution of the pieces. Is it a blocked position with a good your piece his piece ratio (yp:hp) on the side where his king is located? If so, it sounds like a good position for your attack.

Other minor factors include development, opening, material count, and even time control.

Hope this helps a little!

Under no circumstances do I condone pre-meditation of opposite side castling.  It happens when it happens.  It depends on the position.

Saying that you always want to castle opposite that of your opponent, or like another post once said, always looking to castle queenside, is just as assinine as saying that you like Bishops over Knights or Knights over Bishops.  I like Knights when the Knight is better, I like Bishops when the Bishop is better, I like to Castle Queenside when Castling Queenside is my best option, I like castling Kingside when Castling Kingside is my best option, I like Castling the same way as my opponent does when that's best, I like Castiling opposite that of my opponent when that's best, and I'll even keep the King in the center when that's best.

General Principles, like controlling the center, how to attack when castling opposite sides, piece values, etc are merely for a beginner when they are first learning how the pieces move.  Once you are past that, you can throw all that s**t out the window.  It's useless!  I've had games where Two Bishops beat the snot out of a Rook and Knight, even though the Two Bishops are worth 6 in the moronic point system while the Rook and Knight are worth 8.  Guess what?  It's all relative to the position!

Select your openings based on general style of play, but be prepared for the opposite to happen.  There are positional games that started out as a Sicilian, tactical games that started out as a Caro-Kann, positional games that started out as a King's Indian, and tactical games that started out as a Slav.

You MUST remain flexible, or you will fail miserably every time!

Yes, I agree with the poster above.  Flexibility is the quality that you want to condition.  Your question reminded me of a couple of recent blitz games where my opponent was obviously angling to castle opposite.  It telegraphs where my attack should take place!  If I can guess what my opponent wants to do before he can guess what I want to do, who has the advantage?  On the other hand the most irritating players to struggle against are the ones that behave like water -- you push and your push makes them flow around you.  Flexibility.