I'm bias to the first gen when it comes to the Explorer. I like the boxy yet flowing aesthetics, the simplicity and the twin traction beam. It's more truck like than the later versions. It's also fun to watch my alignment guy, (personal friend) go into convulsions when I need alignment work.. He was a mechanic at a Ford dealer when they were new and into the early 2000s. He is intimately familiar with that generation of Fords.
First gens have more influence from older cars in them than the other generations do, and have the most amount of usable technology (electronic fuel injection) compared to older cars, that makes them more user friendly.
I'm a driver, I want control. I could care less about the progression of the feature creep in today's new cars. However, I really like the automatic windshield wipers on my 2011 Mercedes GLK but at the same time, I had a blast putting 200 miles on the Model A last weekend. The first gens fall in the middle of those two, it's something that is as comfortable and simple as it is reliable without having to be babysat. If you've put any kind of mileage on a pre 1930s car, or anything with a carburetor for that matter, you'll know what I mean. There are also 11 computers in the Benz, and I can only interact with the federally regulated parts of it.. it's a techno ticking time bomb that I'm relegated to have to let someone else work on if things go south.
My second favorite Explorer, would be the 4th gen for the body style. They just have a refined and elegant look about them, especially the Eddie Bauers. The current body style looks good, but there is something about them that just hasn't captured me yet. I can't quite pin it down, but the base models that usually make up fleet vehicles, have the weirdest looking grill. If it's not chrome, it changes the whole shape and feel of the front of the vehicle especially when the paint color is other than black. They also are big vehicles. The Explorer has kind of lost the feel of what they started as, (a 2nd gen Bronco 2).
Maybe it's just my old car bias and the fact that I favor smaller SUVs over other vehicles for commuting, but the first gen definitely tugs hardest at my heart strings than the others!