Correct me if I'm wrong but I can't find anything on those reading lists that really challenges the incremental, very slow "change" that Obama prefers.
In general the more sense of urgency a book on Obama's list has the further back in time it was written. Like Obama's health care policy the intuition is always that America requires polishing and not structural changes.
From the Wikipedia on How Democracies Die:
Instead, the authors recommend "forbearance" and some degree of cooperation to keep government functioning in a balanced fashion.
See too much radicalism - that's how democracies die. The idea that democracies die because they stop serving the interests of large percentages of their population is not something Obama can conceive.
Pretty much every book on Obama's list has the same subversive angle. People aren't poor, it's just their perception. Liberalism died because it trusted ordinary people too much. Etc.
I think your reading of Obama's lists as anything other than more hope a dope is just proof that Obama's game remains as virile as ever.