Although it's a luxury SUV today, the Range Rover didn't start off that way and was plagued by quality control issues.
Some of the higher-end luxury cars available will lose you a staggering amount of money over fairly short periods of time, but this is just the nature of this segment, and something you accept when you buy such a car. But when it comes to more mainstream cars, there are some real standouts that might surprise you as bad investments. Alfa Romeo has always been famous for this in Europe, but this could turn around with its reintroduction to the US market. But the Range Rover is a proven money sink.
The first Land Rover was developed in 1947 with the idea of being a useful piece of light farm machinery. All things considered, the evolution from farm equipment to the standard by which all luxury SUVs are judged happed remarkably fast. But it didn't happen right away, and even the earliest Range Rovers weren't really full-on luxury vehicles. Truthfully, it wasn't really a luxury vehicle at all for several years. At the time (1970), the Land Rover Series II was the only other Land Rover, and this was designed to be primarily a military vehicle, but one which civilians could buy if they felt so inclined.
The Range Rover was simply a version which was more practical for civilian use, but not really any more luxurious. Early models had vinyl seats and lacked carpets, air conditioning and even power steering. But the coil spring suspension in place of the more truck-like leaf springs used by some competitors meant that the ride was far more comfortable. Land Rover stressed that the balance of comfort and off-road ability made it a vehicle for all occasions, and it soon started to attract buyers who found this idea appealing. But even back then, Range Rovers were being much more in town than off-road.
The still-excellent off-roading ability served as a reassurance during bad weather, rather than an excuse to drive through mud all day. This popularity with city dwellers would obviously lead to more luxury appointments being fitted, but sales had no problem keeping up with the resulting price increase. Sales got better still when the Range Rover was introduced in the US in 1987, and by the end of the very long production run of the first generation in 1996, the Range Rover had become a very different kind of vehicle. The second generation was basically a refinement of the idea which the first generation of the vehicle had evolved into.
Rather than continuing to add things on here and there, Land Rover elected to redesign the vehicle, this time starting out with the idea that it would be a luxury SUV. This being the mid-Nineties, the SUV segment was starting to really heat up, and the Range Rover would have to stay fresh if it wanted to compete. The debut of the third generation in 2002 brought in a unibody design, thus making the vehicle lighter and improving fuel economy in a segment increasingly dominated by more fuel-efficient crossovers. This all probably sounds pretty positive, and the strong sales of new models should translate into reasonable resale values, but it doesn't.
The trouble with the Range Rover is one of reputation, rather than anything currently afflicting it. Land Rover was, of course, at one time owned by British Leyland, and with this came all of the quality problems for which the company is justly famous. In 1984, the Range Rover had also been fitted with a Lucas fuel injection system, a horrifying thing to come across when shopping for a used car. The Range Rover's quality problems are not what they once were, but it takes a long time to live down a bad reputation, especially when said product is also expensive.