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You are absolutely right - every brand has to evolve. I just think Rapha had that possibility to become an iconic road cycling brand with their own design aesthetic that you can always go back to when you need new kit. Downside of making long-lasting gear is that you need to attract a wide user base to keep the business profitable. They chose to diversify and to me it seems in the process they have managed to dilute the brand message. I may be wrong, but it would have probably been wiser to setup sister brands for their offshoots.
Rox-
The sister brand has become Rapha Core I guess. People know what they are getting there and it is still decent quality, but offers a cheaper entry point. May be some of the misty-eyed nostalgia is misplaced, like the favourite band that you go back to listen to and realise they weren't actually that good.
Squaredisk
Every time Rapha released a new collection there would be vocal cries for bringing back the old stuff. They'd listen, release the merino jerseys and classic shorts that everyone cries for and then shock, nobody buys it and it costs the company thousands.
You're in the minority if you think Rapha kit should still be as it was 10 years ago and that they'd be successful doing that. Nobody is buying that kit. They have to evolve or fail