I think the issue really stems from how the park has developed since the mid-60s.
When Disneyland opened, Main Street led to four lands and four lands only. Adventureland, Frontierland, Fantasyland, and Tomorrowland. Those were essentially sexy names for present, past, fantasy, and future... all of which relate to each other. Like pieces of a puzzle.
Today, we have New Orleans Square, Critter Country, and Toontown in the mix. How do those relate? They really should be listed as sections of the original four lands (like Storybook Curcus is part of MK's Fantasyland), not as their own lands. Another issue is that Adventureland, instead of staying set in the present, is still set in the mid 20th century.
So now Main Street leads to seven great lands that hardly relate. Soon, it will lead to eight great lands that relate even less. This is nothing new. Well-themed lands with stellar attractions have been added to the park at the expense of overall organization since the mid-60s.