My keyboard is very keen on completing “it’s” regardless of context. I imagine this is the case for most people, since usually I see “it’s” when “its” would be correct.

I also think it’s difficult to know that “it’s” is wrong to use because it feels like it follows the common apostrophe for possession rule:
“Australia’s capital is Canberra” -> “Australia is the largest country in Oceania. It’s capital is Canberra.” (wrong, but intuitive)

The comparison is somewhat awkward, because the rails example presumably produces a date, while the python one is referring to an interval of time.
Just from the meme it’s not obvious which was the actual intended use, so labeling either as inaccurate requires us to make assumptions.

Personally, the concept of “10 years ago” is a bit nebulous to me. If today is February 29th, is ten years ago March 1st? Doesn’t seem right. Or particularly useful.