@lithium I'm guessing this is a MUD or some such, and not using TinyMUX/PennMUSh/Rhost. If it is, you might be able to do this all via commands in the game itself.
Otherwise, I think this is your best bet:
https://github.com/potatomushclient/potato/wiki/SlashCommandsAt
You can make a new macro. Name it something like "unequipflyinggear". Then input:
/at now+1seconds=unequip flying gear
/at now+2seconds=unequip flying hat
... etc
Now, in game, you'd enter /runmacro unequipflyinggear
... it should run through each step at the intervals your provided, where "new" is relative to when the first command was used. So, yes, when it they run now will be past, but it's now when you send it.