That's a good thing because newly inserted items didn't prove yet that they are worth keeping.
They have less time to proove themselves but if they prove themselves they can have a long lifetime because they will remain when the hand loops back to tail.
End of cache is filled with items of proven utility. New ones are unproven. Shrinking distance between head and hand reflect accumulation of proven items which leaves less space for unproven ones. Which is good. Eventually (when the space for fresh ones ends) you want to reconsider the proven ones again and this is achieved by moving hand back from head to tail.
It might be unfair to new items comming in at the times when there are a lot of proven ones accumulated but it is a good strategy from the point of view of the whole process. Good solutions are not necessarily fair.
> If randomization of the distance is beneficial, let that be explicit!
But it's better than random. It's adaptive to how many of the items already stored were visited recently.