Kris and Jessica's wedding consisted of them putting their wedding gifts under a pine tree and looking up at the stars, while the Winter Warlock prays for a little magic to make the trees glow. The narrator even notes that "Since no church would have them, they stood before the Lord in a grove of pine trees." So technically...they're not legally married?!
Add to that, their wedding night was Christmas Eve. Which means that Kris leaves Jessica alone on their anniversary every year!
Topper the penguin. Even setting aside the fact that he's somehow wandered near the North Pole while searching for the South, why is he the only animal in the show that wears a scarf?
Speaking of Topper, let's not get into the fact that 'topper' is a weird word for Kris to mutter and then select for a name. But when he's trying to find out why the penguin is where he is, Topper bounces around in a way that indicates he's looking for something. What prompts Kris to immediately discern that he's looking for a word which is synonymous with 'stick'?
If the Kringles were the toymakers to the King of whatever country this is (I'm assuming ancient Germany), how does a Burgermeister, a small-time local lord, go over his head in declaring the Kringles enemies of the state? This bugged me even as a little kid. King > Mayor.
Maybe Burgermeister was a revolutionary that usurped him. That would explain the guy looking like the king without Only Six Faces: The Burgermeister forced him to be an offical.
This was always my interpretation to it too: The King had recently been killed in a revolution where the Burgermeister made himself Dictator of the town. The Kringles had abandoned the town for the woods during the revolution, and survived because of it (Going the long way, not through the Winter Warlocks Domain). In fact, Chris might be related to the original King in some way.
I always thought, just maybe, that while a mortal earthly King is shown, that perhaps the Kringles were somehow toymakers to the King Of Kings when he was a child. But that being too overtly religious for network TV (which cringed at Linus's speech in Charlie Brown) they reduced it to being an unnamed, vaguely-defined King. That, or the King was Charlemagne, ruler over vast parts of Europe, but whom after his death, left his regions breaking up further and further until local bullies like the Burgermeister ruled, and some of them did openly spurn learning and culture.
Kris is trapped in a dungeon. Kris needs to escape the dungeon. The solution? Feed reindeer corn that makes them fly! How does a flying reindeer help him out of a dungeon?!
Maybe it has a skylight that is unseen.
Kris could probably get out of the jail itself easily. But then, where to go? The town is loaded with soldiers, his friends are not all as sharp and fast as he, and the people are cowed for the moment. He needed to get out of town and well away from it as fast as—a flying reindeer.