This Jeep is simply the finest vehicle I've ever owned. It's got ample power, plush comfort, unmistakable styling, and is extremely accessible to work on.
I have found nothing that handles better in snow, and the 360 makes highway driving fun (even though fuel stops come up around every 200 miles).
Those who see past the typical gremlins that can come with older cars make up quite the cult following for these trucks, with a camaraderie among enthusiasts.
It can hold its own against any other of the more modern vehicles in its class (that have the advantage of 30 years of technology) that are currently rolling of the line, and has the added benefit of not costing $30k.
Its styling is nostalgic, complete with vinyl woodgrain trim and plenty of chrome. Finding it in parking areas is never much of a challenge. Also, the wide expanses of glass and slim pillars make for unrivaled visibility. Cargo room is exceptional, and the seats are quite comfortable even on the longest trips.
My only complaint with the truck is its lackluster gas mileage, which typically averages about 10mpg/city and 12mpg/highway when properly tuned. It's understandable, though, considering the classically square body design, and its primitive engine control system. Seeing as MPFI and mildly improved aerodynamics net current fullsize SUVs 15mpg on average, the GW isn't really all that thirsty.
Regular maintenance is essential. Keeping the sheet metal clean will stave off the potentially serious rust that plagues some older Jeeps. The AMC V8s oiling system benefits from regular oil changes, especially at higher mileage. If you keep up with it, 150-200k is not unusual for the high-nickel 360s.
It's important to remember that most of the issues that arise with these trucks are due simply to the fact that they are now at least a minimum of ten years old now, and many have more than 100k on the odometer. The design is inherently solid, and time-tested, as the platform's 30-year run went by without any major changes to the original 1962 design, but they do occasionally require component replacement when parts wear out, as would any vehicle of the same vintage would.
For the most part, the truck is quite accessible to work on, with many parts readily available. The fullsize Jeep line shares enough componentry with both the popular Jeep CJ line and other Big-3 products so that replacement parts coverage is quite good. The truck's older design and convoluted vacuum line system can make finding the right mechanic difficult, as many do not understand the quirks found in older Jeeps, and are unfamiliar with older technologies. So, knowing a little about the truck can be helpful. Quite a few enthusiast groups, such as IFSJA (www.ifsja.org), exist for Fullsize Jeep owners, and are the best sources for solving problems or answering questions without consulting an expensive and potentially unknowledgable mechanic.
I guess that in the end, if you want a truck you never have to tinker with, and can just drop off at the dealer when a problem crops up, you want something new with a warranty. But if you don't mind saving $25,000 and learning a little about the quirks that can come up, and then tackling them, the Grand Wagoneer is affordable, attractive, capable, comfortable, reliable, and an all around blast to drive. Nothing currently out on the market can compare.