It isn't easy to say WHY exactly people like the 1st. Generation Rams, as there's more than one reason. Let me try to make sense of it, from my very own perspective.
First of all, I'm doing well financially, and before I got my '92 D250 half-a-decade back, I had a super crisp '98 Ram 1500 Sport in black with the 360 Magnum gas engine. I had to clean it all the time, as it simply was too pretty. Too pretty for being a truck.
I also am lucky to live in sunny SoCal, so rust is a non-issue for me. My 1st. Gen frame is still black with all factory marking clearly visible and the cab's and bed's undercarriage is still virginal white. Not even a hint of surface rust, save for some washers on the exhaust. (That also means I have no use for a 4x4. )
Personally, I am fed up with computerized vehicles. My cell phone usually breaks before the 2-year service period ends (just did again); my home and work computer crash frequently, and so on. If I could, I would order a new car with air, power windows, locks, and maybe cruise. I don't need, no . . . I don't WANT memory seats, airbags, not even ABS, let alone stabilization control, ASC, ASB, tire-monitoring system, and all those black boxes that will eventually die silently and NEED to be replaced for big bucks.
But I can't buy such a car, or truck. For that reason, new car buyers are trapped in buying new cars, over and over and over again, every few years, and it will only get worse! Who will be able to afford replacing computers and screens in those electronic devices on wheels, a decade from now?
The 1st. Generation Ram, and I have to say specifically the Cummins-powered one, is a non-computer truck. It's an old fashioned truck, featuring a design that goes back to the early 1970s, when they still had metal dashboards and started working on the successor of the Fleetline trucks (of which I have two really nice ones).
But although the 1st. Generation Ram looks like a 1970s truck to the casual observer (especially mine does, as I backdated it sensibly), it does have everything I desire, meaning a/c, power windows and door locks, cruise, and--God forbid--even rear-wheel ABS!
Mine has 180K on the clock now, and has been reliable like a Swiss watch until a few weeks ago, when the injection pump failed (which brought me to THIS Web site).
Although I retired from auto racing (the main reason I bought the '92 way back when), I still LOVE my truck and will probably never part with it. Ten years from now, it will be worth the same as it is today (no rust in SoCal, remember), even with slightly over 200K miles then. What other DIESEL-powered truck would you have to buy, to be able to achieve the same? Is there any non-Diesel powered truck that will not depreciate at an alarming rate as fuel prices continue to rise?
That, my friends, is the reason I love the 1st. Gen Ram. Nice ones, especially with low mileage, will be getting harder and harder to find. That means their prices will NOT go down for a long time. I also believe that the first 2nd. Generation trucks, meaning every Ram with the 12-valve Cummins, will be solid purchases.
It's the back-to-the-basics, no nonsense approach that appeals to buyers and owners of the 1st. Generation Rams.
Just my two cents.