There may be some room for compromise on the matter, but it doesn't seem likely there will ever be agreement. One side of the debate is making a practical case for what they call "competitive equity", in order to minimize (not eliminate) differences in competitiveness between teams within a class. Stonedlizard ought to be commended for the extensive effort he made several years ago in coming up with a system that moves the playoff structure in that direction. The system he proposed can work and likely would reduce competitive imbalances within classes to at least a small degree.
The other side of the debate is taking a more theoretically pure approach to the matter. In their view enrollment is the most objective basis for assigning teams to the different classes. In this thread it appears all are in agreement that enrollment does influence to some degree the relative strength of teams in the different classes. In other words, almost all would agree that the top five teams in 8A would be heavily favored to defeat the best team in 1A. That is taking an extreme example to make a point. However, with the point having been made, the same truth exists to a smaller degree even when comparing classes with smaller enrollment differences (such as 6A versus 3A). I have done a small amount of research on the matter [sample sizes were far too small to be considered statistically significant, and therefore valid] that indicates, on average, there is about a five point difference per class. Enrollment does matter.
The point being made by the theoretical purists is the following. As one moves away from the use of enrollments for assigning classifications, one diminishes the significance (the value of the achievement) of any championship won other than the championship at the highest classification. While it is true the champion of 8A is (perhaps without exception) a better team than the champion of 1A, the difficulty of the achievement (and therefore the value of the championship) is the same for both. The championships in both cases were won in the context of their respective enrollment peers.
To demonstrate the point made in the preceding paragraph an example may be useful. The example will immediately be denigrated as comparing apples to oranges by the competitive pragmatists, but it is sometimes useful to use external points of reference to understand a case. The sport of boxing uses weight classifications because it is understood a boxer's weight influences the outcome of a match. The heavyweight champion will (perhaps without exception) defeat the welterweight champion. However, the victory will not necessarily be due to the heavyweight's skill. It will far more times than not be due to his superior weight (and therefore punching power). It is generally acknowledged that welterweights display superior boxing skill when compared to heavyweights. So, what does it do to the value of a welterweight championship if boxing authorities begin allowing heavyweights to compete in the welterweight classification? It devalues it. The championship was not won through superior ability, but through superior weight. What does it do to the value of a 5A football championship if the IHSA begins allowing 8A schools (based on enrollment) to compete in the 5A classification? The theoretical purists argue that it will devalue it. At least some of the 5A championships will no longer be won because of the development of the skill of a team's players, or conditioning, effort and coaching, but, instead, some of the championships will be won because one school had far more students than the other.
That is the trade-off; competitive balance versus championship integrity. Perhaps some compromise could be achieved, but there will never be total agreement as to which of the two objectives is more desirable. Both sides of the discussion have merit.