A big part of the reason for more expensive service for more expensive cards is the grader's liability while in possession of said cards. If they lose or damage your t206 Wagner or 1952 Topps Mantle they're on the hook for a little bit more than if they lost or damaged your Wade Boggs Rookie.
As for your thoughts about trying to estimate the grade to declare a value, I feel a LOT of people make this mistake, and some people even think that their estimate affects the final grade they receive.
In my experience this has no basis in fact. My declared value always reflects what I would need to be made whole if the cards were lost or damaged in transit and in no way reflect the value I hope to achieve after grading. I have never felt this has negatively impacted the grades I have received and often my declared value has been several multiples lower than the value for the grade eventually received.
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