It takes five days for the Howling Commandos to find Steve after he was captured by Hydra. By then Hydra had tortured him to the point of delirium. That doesn't dissuade the army from putting Steve back on the front lines when he's recovered. He'll heal, right? Bucky watches Steve represses it and they don't deal with it until he and Tony are captured 70 years later.
The Time Keepers (or whoever is in charge of the TVA) miscalculated when they decided to send Steve Rogers back in time and thought he wouldn't try to change things. Loki finds an unexpected ally.
Tony and Steve team up to fix the engines after an initial clash on the Helicarrier. It's going well until Tony finds Steve dissociating after his near fall out of the Helicarrier fighting Loki's goons. It isn't what he's expecting, and Tony has to confront the fact that Captain America isn't what he first thought.
The song "I'll be home for Christmas" was written in honour of soldiers fighting away from home during World War Two. It's a letter from a soldier to his family back home. Steve and Bucky listen to it on a freezing Christmas eve in the middle of a French forest far from home.