I've only had mine 5 months so can only give you a few pointers which probably apply to many other cars too.
Things to keep an eye open for:
1) A slight shudder when pulling away in first or reverse. Could indicate the clutch will need replacing soon.
2) Cracks in the plastic headlights can let in water leading to fogging.
3) For the saloon with the boot up open the flap behind the lights. Water might come out indicating the rubber seals around the light might need replacing. I think these should have been done as a workshop action on the early B8's but mine wasn't. Also check the spare wheel well for water.
Apart from that it's a great car and the engine is sweet.
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