I'm not sure I follow you at all. Why would logic dictate older readers would prefer his older works? I agree with the notion that the Constant Reader (or any reader) will do better to cast assumptions aside and sink into each new story. I just don't think I am understanding the rest of what you have to say.
I'm just suggesting that since older readers were alive when the earlier works came out they might hold a preference for them for a reason such as nostalgia.