1. I only recently discovered the road via Helgen, Orphan's Rock and Haemarr's Shame that leads to Ivarstead. I've always gone the long way around (ie, by Valtheim, Dark Water Crossing, etc).
2. I hate Dwemer ruins. Every other cave, cavern and ruin I will explore every nook and cranny. With Dwemer, I am in and out in as little time as possible. It isn't a fear thing, I just find them very tedious.
3. See above for the Soul Cairn
4. I usually main quest up to Diplomatic Immunity and then do a load of side/guild/radiant quests. Then get annoyed when I have too many quests and start a new character. Rinse, repeat.
5. Wispmothers terrify me more than any other mob in the game.
6. I only recently understood what Delphine means by, "you should know, you got the dragonstone for me" (or whatever her exact line is). In all my characters, only recently have I been to Farengar before Bleak Falls Barrow.
7. I never side with Sven. Ever. He seems like a "milk-drinking" mummy's boy, and he bugs me to hell and back.
8. It took me 4/5 starts to realise I could follow Hadvar into the keep, and only a little time later did I realise my choice of sides in the Civil War wasn't locked in by whom I escape Helgen with.
9. Recently discovered the extra dialogue if you reach and speak to Alvor before Hadvar arrives. Similarly, only recently discovered the extra dialogue if you exit the conversation with Irileth when she grills you, and go straight to the Jarl