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In the end felt more comfortable buying a newer bike that was coming down in price than something 20+that was almost the same value.
I'd do the same if I was in your position.
For now the ship has sailed on all those old bikes.
Moreover they're bikes that are going to get knocked about. It's a long way from say an old litre BMW.
I too really struggled with this when realising an XR400 isn't a £1.5k bike anymore. In the end felt more comfortable buying a newer bike that was coming down in price than something 20+ that was almost the same value.
I think being a bike that will have been, and will continue to be dropped etc makes this all even harder to process. My CRF450L is brilliant, but also cost 6.5k so yeah it's a hard one.