There are 3 things in play when it comes to range:
1) Actual range loss due to battery degradation- This is to be expected as per Tesla. It's understood to be most significant early on in battery life and then taper more gradually over the remaining life of the cells.
2) Temporary range loss due to pack imbalance- This is a known issue with series style battery packs such as Tesla's. The loss is real in that the total pack range is diminished until the pack can be rebalanced. It's understood that the Model S can re-balance the pack, but when and under what circumstances is not completely known. Once the pack is in balance the range is restored.
3) Apparent range loss due to algorithm inaccuracy- This is simply visual inaccuracy due to the fact that "at rest" estimates of battery capacity are calculations, with a number of variables (temp, cell age, etc...). The greater the extremes of charge and discharge, and thus the larger sampling extent, the more accurate the algorithm may be. The converse is that shallower charge cycles result in less accuracy.
As I've written before regarding issue #3, because of the evidence supporting the concept of shallower charge cycles being better for the pack, I don't believe it's worth attempting to charge or discharge to greater levels than necessary just to see a different number on the dash with issue is worth it.
With issue #2, the range loss can impact a person if they really need it, even if for a single long trip where you are really pushing your range limits. If you really are down to counting a few extra miles to make your journey it may be worth-while to try and force a pack rebalance. Anecdotal evidence suggests this happens at the tail end of range-charges (where the last percentage point of charge can take an hour or more). As range charges are harder on the battery, I recommend this only if you have no other alternative. It's uknown to what extent the Model S attempts to balance at <100% charges
For issue #1, it's a fact of life with Li-ion cells. However, given that deeper carge cycles, time at 100% charge state, and high temps are all hard on the battery, I make the above recommendations with the aim of minimizing this real degradation.