I think you have probably hit the nail on the head re cachet. As good a car as the 306 is, and objectively a better car than the 205, it just doesn't have the same cachet.
Certain versions, such as the GTI 6 and the Rallye, will probably go up in value, but it is doubtful they will ever get as high as the 205 GTI. So the 'less desirable' specs certainly won't, though they may increase slightly. It is the classic 'hot hatches' where the big money is to be made, where folk (usually men) growing up in the 80's, lusting after cars like the 205 and Golf GTI, now have the money to indulge in the same way that a couple of generations ago, it was cars like the MGBGT. But none of those buyers will have lusted after a lower spec version, so they will never reach the same prices. There is a 205XR on Ebay with 4k miles from new, dry stored, up for £5749. Which is quite a lot of money granted, but probably a quarter of what would be asked for a GTI in that condition with that miles.
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