A very interesting topic that can certainly be twisted around from different perspectives! Indeed, i think it is a very general problem in foundational physics to find objective observerindependent measures. And information measurems or probabilitiy measures are certainly at the heart of this. I will refrain from commenting too much as is risks beeing too biased by my own understanding.
You seem to circle around a desire to formulate a conservation law in terms of principle of least action? Then note that we have the
Kullback-Leibler divergence (relative entropy, [itex]S_{K-L}[/itex]) wose minimum can be shown to coincide to maximum transition probability. A possible principle is then to minimize information divergence. The statistical weight in case of a simple dice throwing case puts this into a integration weight of [itex]e^{-MS_{K-L}}[/itex]. You find this relation from basic consideration if you consider the probability of dice-sequences. The factor M is then relted to sample sizes. So we get here both measures of "information" and "amount of data" in the formula.
But when you try to apply this to physics, one soon realizes that the entire construct(computation) is necessary context or observer dependent. This is why relations between observers, becomes complex. Ultimately i think it boils down to the issue of how to attache probability to observational reality of different observers.
So i think this is an important question, but i think one should not expect a simple universal answer. Two observers will generally not in a simple static way agree of information measurems or probability measures. Instead, their disagreement might be interpreted as the basis for interactions.
Edit: If you like me has been thinking in this direction, note the intriguing structural analogies to inertia. Sample size seem to take the place to mass or energy, and information divergence that of inverse temperature. Then ponder what happens when you enlarge the state space with rate of change, or even the conjugate variables. Then the simple dissipative dynamics turns into something non-trivial - but still governed by the same logic.
/Fredrik