For the most part, item changes are easy (as you note) and thus are likely to follow the timeline. For example, the Cleric mask with Call of Bones will be nerfed to a Fear effect right before Kunark goes live (Nilbog is already aware of this and planning on nerfing the item accordingly).
Spell stacking issues are a bit tougher, some even more than others (like DoT stacking). That being said, if the devs can be made aware of exactly how it worked before the change, when it was changed, and why, it's likely that an effort will be made to mirror classic as much as possible. However, there are fewer resources available for making core 'code level' fixes than there are for things like item, spawn and quest fixes, so code level changes will take longer and have to be prioritized more carefully.
To the topic of shrink spells, another fix that should be made is to modify Ant Potions to have a location restriction as well, although that gets removed in Kunark (July 19, 2000, a month after The Hole went live).
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-Bumamgar
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