These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
"Funny Aneurysm" Moment: There's a scene where Irv Blitzer clutches his chest in exasperation. John Candy died from a heart attack five months after the film's release.
After the Jamaican team's third bobsled run at the Olympics, the East German team captain congratulates Derice with "Very good, Jamaica. See you in four years, ja?" Ironically, that wouldn't happen, because while Jamaica did return to compete in future winter Olympics, East Germany itself ceased to exist prior to the next Olympics in 1992.
Older Than They Think: Several tropical countries, not just Jamaica, competed in bobsled in 1988, where they created an informal "Caribbean Cup". Mexico competed in bobsled in 1928, the second Winter Olympics, so the phenomenon is Older than Television.
Unfortunate Implications: Avoided with the Jamaican protagonists, but played uncomfortably straight with the bullying German team, who are excessively disciplined and abusive towards the Jamaicans, with some pretty heavily racist overtones.
What's equally unfortunate is that this is NOT how the other teams behaved in Real Life. They were actually very friendly and willing to share the use of their sleds and other equipment in order for the Jamaicans to prepare for the competition.
Irv lampshades this by asking the Alliance if four black guys in a bobsled makes them uncomfortable.