Entirely agree, although I think it varies by make / model. Roughly look for whenever a particular car got OBDII, which makes diagnostics way easier (and was kinda the perfect level of digitization, again in my opinion), through (as you say) whenever they started digitizing the cockpit and/or (which oddly - maybe? - coincide, in my experience) manufacturers stopped considering ease of maintenance in engineering decisions. In general late-1990s through 2005-2010. Cars since that decade (or so) are more sophisticated, at the expense of far, far shorter useful lifespans.

Depending on the make, rust-protection wasn’t quite there yet.

4th gen 4Runner w/ a 2UZ-FE

Still got my E46!

I've got a supercharged E92 M3. I'll own that thing till I die, funnest car ever.

Nobody is currently selling new, small pickups. Maybe if the Slate materializes, that'll prove the market and we'll see them again.

In the meantime, 200x Ford Ranger or 200x Chevy S-10 are the last of the small pickups where you can get a 6 foot bed and a single row of seats. (Afaik)

I sold my small white pickup once, and ended up with a different small white pickup a few years later. I do enough (small) truck things that having a truck on hand just in case is worth it for me; but even with minimal miles per year there's certainly added expense from maintenance some of which ends up being time based, registration fees, and incremental costs for liability insurance on another vehicle. For quite a while, my family vehicles were a 4-door car/wagon and a small pickup, but that doesn't work for everyone; I feel better served with a minivan, a 4-door phev, and a pickup (and a silly old rear engined vw van with only the front seats, mostly for midlife crisis, but also handy for picking up large items that don't want to be inside for transport)

I've felt similarly recently, and I think those days are fleeting if not gone. Ford recently talked about replatforming their entire range, which would include basic trucks at more reasonable prices, but there's not really a market for work trucks in the way there used to be, and they're gone in favor of the luxury ones with small beds. It is annoying. There is an interesting startup that I can't remember the name of that touts an 8 foot bed (which is great) in the chassis footprint of a Mini Cooper. I don't think I saw pricing, but I would snatch one of those up.

CAFE standards have made that pretty hard. The trucks got bigger to hold more complex engine setups to boost mileage, coinciding with preferences shifting to super crew cabs because buying a new truck is basically the same price as buying a luxury vehicle.

I did own a 1994 Dodge ram up until a few years ago, but it needed new brake lines and there was so much rust coming off the frame I honestly wasn't sure I trusted it anymore, and the cost of the brake lines was probably more than it was worth at that point.

Maybe Slate? https://www.slate.auto/

A new 1980's mini truck would be awesome. If only...