Here is a position that cropped up in a game I played recently. I have a couple of questions; which way should I have castled and how do you decide which side is best for castling? In the game I reasoned that black had less pieces king side and so I castled short. This was more of a guess than anything. Any pointers would be appreciated
I would have castled kingside too. A couple other reasons that would sway me-- Black's King is currently Queenside and can't castle, so I'd like both of my Rooks Queenside without my King in the way. Also, even though it's not a problem at the moment, the pawn structure leaves the White Queenside back rank vulnerable to diagonal attacks, and Black still has both Bishops. If you castled Queenside right now, ...Bg5 would lose you your Queen.
EDIT: Whoops, no, you could play f4 to save your Queen, but the diagonals are still a problem down the road.
First of all, 0-0-0 does not lose to Bg5, since white plays f4. Still 0-0-0 does not appeal to me. I agree with Florisz' assessment, play Bf7 ad get a decent advantage, and keep your king in the center for now.