I’m always a little bit mystified by the whole “cult of Gary” in terms of advice and processes. Not only is his advice often contradictory, but it feels vaguely like trying to improve your baseball team by rummaging through archives looking for advice from Jimmy Collins or trying to build an airplane by reading interviews with the Wright brothers. Anything you might find is very much a product of its time, at best, with an added layer, in Gary’s case, of not even necessarily reflecting how he did things at the time.
It’s just odd to me that so much importance should be placed on the opinions of someone from so early in the hobby, as if being the first person to do something necessarily makes you good at it.
All that said, I think the biggest problem with timekeeping in RPGs (and, come to that, with a lot of things in RPGs) is that no explanation of why it is useful is ever provided, which is even more strange and baffling to me considering how many RPGs not just allow but encourage the GM to change the rules to “fit their style” or the like. Timekeeping is critical for certain applications and utterly useless to the point of being detrimental in others, but somehow, game designers expect GMs not only to pick and choose the rules for their games, but to do so without any explanation of what the purpose of those rules is. This is especially visible with things like wandering monsters and encumbrance, which have often become vestigial (as mentioned above) but are retained anyway, or which are perceived as vestigial, but which should actually be used for certain types of play. But rather than be able to find that out by reading the game, people have to scour the internet for “GM advice” and then sift through the reams of it in an effort to discover what’s relevant and/or helpful.
So basically: If we’re going to continue to use this whole “It’s really up to the GM!” approach to “game design” then we need to provide the GM with the information they need to make informed decisions about things like this. And Gary never did.