Perhaps reading the book 'art of attack' by Vukovic helps answer this question. The book shows 'scientifically' the methods of attack against the king in the center, castled on kingside and castled on queenside. Knowing all these attack patterns can make it easier to make the right decision. I have not read this book yet so I can not say for sure, it's a guess.
Which side to castle in the Sicilian Defense?
I think O-O-O is a attacking move and O-O is a defensive move... A long time ago I had the pleasure to make the move O-O-O#
Seriously?? That’s super cool. I’ve always thought that would be the coolest possible way to checkmate. Can you post the game here? I’d love to see it.

Seriously?? That’s super cool. I’ve always thought that would be the coolest possible way to checkmate. Can you post the game here? I’d love to see it.
In Lasker vs Thomas, White deliberately passed up an opportunity to 0-0-0#
http://www.chessgames.com/perl/chessgame?gid=1259009

I think O-O-O is a attacking move and O-O is a defensive move... A long time ago I had the pleasure to make the move O-O-O#
Seriously?? That’s super cool. I’ve always thought that would be the coolest possible way to checkmate. Can you post the game here? I’d love to see it.
I do not have this game anymore .
But it's not as sexy as it looks (does it look sexy anyway? lol). My opponent did not resign (I had a huge material advantage) and decided to walk with his king running away from checks. I had already read about O-O # (or O-O-O #) and the story of Lasker (the weak one) vs. Thomas so I decided to deliberately push his king into a O-O-O # position. In other words, it was very artificial, since I could have given mate before in various ways, but I manipulated my queen checks until I reached the ideal position to make O-O-O #. Understood? Something like a 8 or 10 checks, not a real combination!
I think O-O-O is a attacking move and O-O is a defensive move... A long time ago I had the pleasure to make the move O-O-O#