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Keep in mind that modern Land Rovers are completely different beasts than the "classic" pre-2005 ones. The newer ones are thoroughly modern vehicles with lots of luxury features and current engine technology; the older ones used technology that stretches back to the 1960's.
I have a 2003 Disco 2 with 158K miles. It has been my reliable daily driver and weekend off-road and ski vehicle for many years. The reputation these vehicles have for poor reliability is not entirely justified. They are not unreliable, but they are definitely very maintenance-intensive and demand an involved and observant owner. They are not a good choice for someone who doesn't want to do some of their own wrenching and stay on top of little things the truck needs, or invest in the proper fluids and parts. A good independent mechanic to handle the rare bigger jobs is also mandatory. Don't take them to a dealer, the Land Rover dealer service departments are notoriously awful and overpriced. Fortunately, for all of the known weak spots, (such as the "3 Amigos"), there are known and usually very simple solutions.
If it's in your price range, I'd look at a newer Range Rover Sport as a winter commuting car and skimobile. (Despite the name, it doesn't have much in common with the full-size Range Rover model.) The interior is gorgeous, it's quiet and comfortable, and even though it's the model that's not marketed toward off-road use it's still better off-road than the SUVs from most other manufacturers. Put some good winter/snow tires on it and it will be nearly unstoppable in bad weather.
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