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@clubman
Why aim to ride in a group with strong riders?
It makes you work harder.
It develops your technique, both because you are forced to refine your style to economise on effort, and because you have the opportunity to observe the skills that the others have already perfected.
With any luck it helps to create or strengthen relationships, which are a major part of what this game is about.
To go back to Boucher and Anquetil for a moment, Jacques was the strongest rider around, so unable even to train with his equals, he would ride behind Boucher's Derny pacer.
To answer mdcc tester's point about the need to have similar abilities, I'd say that once you have mastered the technique of group riding, which is basically being able to follow a wheel, it is quite possible to have a range of strength within a group. The better riders do more work at the front.