Yes! It was a trick question indeed!
Nah, I didn't provide enough details that was my bad. When I was checking out the boots in-store I found that sizing down half a size was the most appropriate choice, not realizing that I was wearing no-show socks with my CP's at the time. So a month and a half later I purchased a pair online, naturally thinking that I should size down (from a 9 to 8.5).
When I got them I found the fit to be rather narrow not even with thick wool socks but merely average crew-socks (albeit no problem length-wise). So I'm reflecting on whether I should have stuck to my normal size. That said, if the leather on the 1000 mile boots do tend to stretch more as you've described, then it may still accommodate my foot in the long-run.
Red Wing Beckmans and Iron Rangers seem to fit me just fine in US 9's, though they also fit slightly narrow to start (even with my normal size), but I digress.
Thanks for your reply, cheers.