I'm asking this again a year later. I just feel like they are about to go from junk to cool because you grew up with one. My son recently bought a nice 2000 Ford Expedition. We had one as a family vehicle then I gave it to him when he turned 16. It was black and had some fairly big tires on it. It got T-boned. Now at 31 he bought one. I knew it was going to happen since it was his first car and they are so damn handy to own. 3 rows, 4WD, you can tow with it etc.
I fully expect my daughter to buy a first gen yellow Xterra since that was her first car. My kids are car people, like they ever had a chance not to be!
The first ones were really the Bronco 2. Those already are collectible. The Square Explorers might well get there, even 4 door, because they look 80's. Kind of like the square S10's now.
2 door Blazer/Tahoe is up in price because it is the GM version of the Bronco. Broncos have been up in price for a decade now. Ramcharger lagged behind but recently has exploded. I mean, so far as a truck will, more like went from $3500 to $10,000. Still....
Late 90's? Eh, I dunno. They made a gazillion, and most people that grew up with them had 4.0 4wd Exploders, not the Mercury or high optioned Ford version with the 5.0 cobra motor and AWD. So most people that grew up with them, hate them lol.
Full size SUV will always have a market. Not probably collectible really, just that a new one is like $90,000 so old ones get a boost just because people want one and don't have mortgage money for it. i owned a '98 Expy with NO air ride, but the 5.4 and heavy tow package suspension etc. Ultra reliable, ran it for years, sold it with 180k miles on it with a small manifold exhaust leak. How to fix the leak? Take off the wheel, fender, inner fender, and maybe the shocks i think, so you can access the exhaust from outside. Or pull the whole motor. Power steering leak? Box is bolted to frame. Hoses connect to box between frame and box. Bolts to hold box on are from the OUTSIDE of frame. How to get at sterering box then? Pull motor, or remove entire drivers fender. To replace a leaking PS hose.
I sold mine. You have to be some kind of dedicated Ford boy to want to repair that kind of BS, and by the time I got to this point I was no longer interested in "modular" Fords. I replaced it with my '13 AWD Hemi Charger. Won't be fixing that either.
New era cars make for terrible old cars/collectibles. Too much BS, too much computers that will go bad with no support for replacements, and no way to go make one in a machine shop. Late 90's for CERTAIN VEHICLES is about the cut off I think. After that globalization ruined most interesting car characteristics. maybe the vettes and such will hold their own, but they still have computer issues to overcome.
For your case? I would run that thing into the ground with a rumbly exhaust and enjoy it. It isn't a retirement savings type of car, very little of anything after the front wheel drive revolution is, and most are Japanese.