Do you think a Rover is a "pretty" car?
On occasion. Nothing serious though. We also have pretty brutal winters up here in the hills of CT with a pretty bad snow removal department. The 4wd comes in handy.
What model and what year?
There are many things you need to look out for. Lets start off with engines. Any Pre 03 Range rover or 04 or earlier Discovery has a Rover V8 engine derived from a 1960's buick motor. Both the RR and Disco are very similar vehicles. They're inefficient and loud. They tend to leak, a lot, especially over time. Head gaskets, valve covers, main seals, you name it, they can leak. Headgaskets obviously are the worse and although not common in every land rover, they are not unheard of. The cooling systems are pretty bad too. They leak as well, oil pumps in 03 discoveries are notorious for dying. Cooling system failure can also lead to destroying your engine. In these models door locks and windows are also pretty unreliable. They tend to break a lot. Electrical systems in general aren't great, especially in the pre 03 range rover which tends to have lots of computer issues. I would avoid any discovery with Air suspension (Range Rovers have it stock though many convert it to coil springs) because all it does is break. An air spring will leak, run the compressor to death, and then you have $900 in parts alone + labor + the $75 to clear the fault code. Power steering leaks are common in the Range Rover Classic and Discovery 1 (1994-1999). Sunroof leaks are pretty common too. Driveshafts and U-Joints are very likely to die too.
So yea, basically anything that can go wrong does go wrong. I will say that they have very good transmissions and A/C equipment. My parents have owned a 1963 Series IIa, a 1990 Range Rover Classic, a 2004 Discovery SE-7, and a 2007 Range Rover Sport HSE. I used to have a 1998 Discovery LSE but now I have a 2000 Discovery II. They're not reliable at all, but in my opinion they are the only remaining manufacturer of real SUVs (notice there are no 2wd Land Rovers being sold unlike jeep, toyota, etc). A 2wd SUV is as good as a station wagon, only the station wagon is probably better in the snow because it probably has FWD. LR has changed much from their original intention but still hold onto their heritage.
Let me know what year you're interested in and I can help you out a little more accurately.