I do think that context is still important in general, but probably only if you're doing deep research into Macaulay (or the specific target in mind). Treating everything in a vacuum isn't great either. Plenty of philosophical works for example, you really have to read in the time period and in the context of the author's life.
I find an acceptable tradeoff for now is, if I want to do deep research for myself, opening myself up to this sort of mushy subjective stuff is actually really important for making deep, objectively correct observations. Especially if the goal is to steelman, not strawman, the opponent's argument.
Otherwise, this kind of worst-case analysis thinking is fine. It's a logically sound conclusion, it's just kind of unsatisfying because we can't make stronger claims.
How do we decide when to make this tradeoff and for what things? Uhh.... idk. For me though, there has been value in using both kinds of thinking before though.
On a public forum, worst-case analysis is probably fine because the discussion ain't that deep. Also probably 90% of comments are made within the intention of a "gotcha" and not actually for discussion.
Basically, I totally agree with this, it's just that I've seen one too many online forums devolve into thought-terminating cliches using "rationality" as the basis. Here, I think it's totally justified to take this line... I instinctively had the same reaction upon reading GP's post (but then you could argue it's tone policing... and ahh we're off to the good ol' internet debate race spiral)