A lot of people say that about temperatures - I think it's a mix of acclimatization as you suggested, and the level of humidity in each area. When it's subzero here, it's bone-dry: virtually no humidity. To illustrate why that's important, imagine that you have long hair and you take a shower. Then while your hair is still wet, you go outside into the cold air. You're going to feel colder than if you had dry hair. So I think when it's 20s and a little humid, it's understandable that some may find that to be colder than -20 and dry.
The weather here is wild in that it goes between 90ish in the summer to -40ish in the winter and what I consider to be "cold" at any given point in the year varies wildly. Right now, when it hits 20 degrees, brrr! But in a month or two, if it hits 20 degrees I'll be thankful for the relative warmth. My first winter here, we went months without hitting 32 degrees and when we finally did in March, I was in a t-shirt while shoveling snow
And the same is true for the other end of the spectrum. When I first went SW a few weeks ago, and stepped into 90+ degree weather, it was a shock to my system. It took about 3 days before I stopped feeling weakened by it. By the end of the trip I was
loving it. And when I got home to 50 degrees, I was layered up like a triple-layer chocolate cake.
ETA cool about your job at Sagamore