OD&D and "Never Split the Party"

OD&D and "Never Split the Party", you know the trope - never split the party and many players and DM's believe this is the only way to play and resist any split. However, the truth of the matter is that there are many times when splitting the party makes a lot of since and is the smart thing to do.

Now bitd we always had someone scout ahead, because someone always chose leather armor and when thieves were introducted those same people usually placed thieves. Since our group back them was 12-18 or more players we always had at least 2 thieves and once we had thieves they always scouted ahead.  Sometimes we had as many as 4 thieves and we would send them out in four different directions to scout and report back and sometimes we sent them out in pairs.  Granted the larger the party the safer it is to split into two groups. Bitd we would split into two groups and attack from two directions among other things.

Even now I always think it is wise to try to have someone scout ahead. Currently I don't have thieves in the game - that is a story for another time - so we have whoever is best equipped do it. For a few years recently we had a player that was running a 1st up to 4th level dragon and he was always flying at high altitude scouting ahead.

Splitting the party for these kind of things always seemed to work well more often than not. However, in the Ruins of Murkhill campaign, my one player who started playing when he was 16 and came from an MMO background was always splitting the party by going off on his own and that did not always work out so well. The other players were very good about it too, they would sit back when he did it and would not give him suggestions or advice, but would let him get himself out of it, if he could. They would usually wait until he had been gone at least 16-24 hours in game time before they would look for him. I asked him once, "Why do you do split the party like that when it does seem to work very well for you?" and he replied, "Because such interesting things happen when I do it!"

What are your experiences with splitting the party?