I've owned Audis now for 25 years, and they have always served me well. I have never had any major failures, and the minor failures have been nothing more than temporary aggravations. I will say that one failure stranded me - my 1990 Audi 80 quattro had a fuel pump die out in the middle of BFE. That sucked pretty hard.
But it was a pretty cheap and easy fix, so I was only disgruntled about the location of the failure.
I have found that working on the cars is a bit of a challenge if the cars have spent any time at all exposed to salt. Suspension bits that are all rusted together don't like to come apart, oddly enough.
Because winters around here involve snow and ice, the AWD system that Audi sports really does wonders. Paired with real snow tires, these cars are top-notch when it comes to winter. Sweet heated seats, AWD, power everything - and the prices on the used cars are damned nice. If you can find a good, used Audi, you can drive them until the wheels fall off. I usually drive mine 100-150k before I sell them.