So glad to see these great questions and thoughts coming in. Thanks!
@Skylar, that sounds like more of a business process question? I’m not sure I quite understand, but I’ll say I’m not a business person, so add a lot of salt to anything I say on this. But I will add that rewriting copy for a small section of a web page or an onboarding screen for an app (this last is indeed non-trivial, as www.useronboard.com and my own experience attest to), but if it’s a matter of copy, try getting a cross-team group together in a room for an afternoon to brainstorm around the copy; keep in mind who the users are and what they’ll want to do. That part should not take weeks.
@Jack: Ha, thanks for the reassurance! And indeed, familiarity is a design element, and argument by hyperbole can be useful. I do hope these heuristics, as they evolve and are refined, can also be of use in checking design decisions that might potentially be… less savory.