Want to know what cars are going to be huge in 30-40 years? Look at what kids drive and what they want to drive. If it’s what they drive and fun, it’ll be a classic. If it’s slightly out of reach but that rich kid of the school got one when he turned 16, probably gonna be a classic. The downside? In 20 years, it’s not going to be a classic. And in 60 years, it’s going to drop back down. Today’s classics are almost always invariably the cars people in their 40-60s range loved when they were kids.
A running/driving pickup truck will always be able to find someone that loves it. Make, model, year, equipment. The only thing holding trucks back are rust and emission laws. Numbers matching really isn’t a thing, V8s are always a plus but not even that is required. Stock or modified? Whatever. Regular cab short beds tend to have the most “collector” value as they have a kind of “free spirit” attitude to them. However their market really isn’t a collector market. People buy old trucks, clean them up, and use them. Nobody flips trucks like they do cars because there is no money in it. The truck market is one of “love of the type” vs “love of the model”. Even old pickups get used as trucks regularly.
These tend to “die” when their operating costs exceed their income potential. Rare ones do get restored, some are left in “as is” condition and just mechanically restored. But cases of these are pure labors of love. Someone sees a truck, falls in love, and cares for it. No profit is going to be had here.
They tend to be stable as a whole, not really gaining nor losing much value as their value is tied more into how the economy is doing compared to the year since a large section of the market sees these as pure unobtanium.