I'm also into Model T's, so I have watched a bit of what the sunsetting of the hobby looks like. People have been predicting the death of the Model T hobby since the 70s. I'd say it peaked between 2000 and 2010. With some exceptions, the decline in value has really just been inflationary. A car worth $10k 20 years ago is still worth $10k today. They really haven't dropped in price, just haven't kept up with the decline of the dollar.
The big problem in recent years has been parts availability. The T hobby was well supported by many boutique shops making aftermarket parts run by people in the hobby, not corporate entities producing parts in China. This was great for a long time, until they started aging out of being able to produce the parts, and unable to sell the business because everyone else in the business was at an age they wanted to reduce their workload, not add to it.
Musclecars are different, though. They can be driven with modern traffic, even in completely stock form. They'll never be as inconvenient to use as earlier cars. A bone-stock Chevelle could be daily-driven comfortably, and actually handle reasonably well with just tires/sway bars/steering box upgrades. People using the earlier cars as an example of declining interest are forgetting how badly most of the cars up into the 50s drive.
Another factor is dillution of the hobby... An enthusiast today has 120+ years of cars to choose from.
There's a million ways this can go, but I don't think the hobby will crash or die any time soon. Becoming more affordable for the next generations isn't a bad thing.
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