First I am NOT a Reagan fan. I was not a fan of Arnold Swarzenegger either and for the same exact reasons. Yet there were great commonalities with their rise to political stardom. If one looked at actual qualifications for office such as formal education in profitable areas neither man had the qualifications necessary to hold office.
People without the proper qualifications are easily manipulated by advisors who at times are little more than front men for special interests. Reagan was in some ways his own biggest fan. Ronald Reagan turned both the Governorship of the State of California and the White House into his two greatest acting roles.
By the way I like your list of reading material, but my personal feelings are that none of this writing captures the essence of "how" but focuses on the failures and the deceptions he sold to Californians first and most of America later.
There was not really from my own research over the years much about Reagan that was real. Much like General George S. Patton, Reagan created a bigger than life image and then with speech writers more talented than most of his screen writers he began the job of convincing the American People and particularly those of an ultra conservative mindset that he was something far better than any of their other alternatives.
Now all that being said, your question was in regards to Bill Maher's flawed comparison of Reagan to the average "Teabagger".
Teabaggers these days simply ignore the truth and when they don't get what they want they use very blatant tactics including but not limited to obstructionism, smears, character assassination, and scandal to get their way. Listening to these people rail on and on and on spouting incorrect information as fact and living in a vacuum that does not relate to the real world was not Ronald Reagan.
Ronald Reagan knew very well how to go in through the "back door", charm the birds from the trees, and make total baloney look like absolute brilliance. This is a very large difference. Reagan was an expert at "back door politics". Reagan had finesse which is a total contradiction to "teabagging".
I actually like Bill Maher and he is at times a more than competent comic and he has done some decent work in the political arena. I will never take that away from Mr. Maher because he has worked hard to accomplish what he has and has earned is place.
Success of a President these days is not always measured as it should be. Ronald Reagan left behind multiple legacies, and one of the largest was his ability to cover his failures.
Reagan was successful, had Richard Nixon been as successful there never would have been a Presidential Resignation.
With regards to individuals in the White House in spite of his failures I do not see Ronald Reagan in the same light in which I would view George W. Bush, Jimmy Carter, California Governors George Deukmejian, Pete Wilson, and Arnold Swarzenegger.
In more recent years I would view the Presidential Administrations of George W. Bush, George H.W. Bush, and Richard Nixon in far more harsh lights than Reagan.
There are many words not of a complementary nature that I feel could be used to judge Ronald Reagan, the word "Teabagger" is the only one that I disagree with. Slime Ball yes, "Tea Bagger" no.