It doesn't sound like you were there in 1955
To paraphrase Lloyd Bentson, "Mr. Gray, I knew Disneyland (in 1955), and you don't seem to have been there." For us kids, it was the next step beyond Knotts Berry Farm--incremental as you say. But the television channels is academic gobbledygook--why do we do that? It was experienced as a way for Disney to package their entertainment stories (unless you have memos or something, I would drop the TV channels theory--if it is true it went right over our heads!).
The criticism about fake diversity, no competition on Main Street, etc. I guess, but none of us ever expected anything different. Even as kids we knew that this was an amusement park, not a recreation a la Colonial Williamsburg or some critical commentary on how we should be as a society. As to the underground activity--the Atlantic City casinos do not have legal prostitution or drugs, and it is not legal on Main Street either, which is not to say that they are not available if you know how to look for such things (even a teenager willing to leave the marked paths can come across such things).
The real lessons of Disneyland are not about the veracity of style, they concern crowd control and keeping the masses happy. Set you critical insights toward what Disneyland's design has to say about post-9/11 America and we might all learn something important.