It's a good one, but it helps to have great source material. I think the most surprising thing about the early chapters was how different slavery was from my conception. Though this is no doubt due to Douglass being in Maryland within throwing distance of the Mason Dixon line, rather than in the Deep South. Rather than working for years in the same field, he moved around quite a lot, both with the family that owned him, but also being 'rented out' to other families who needed labor. Later on, he learned a trade in caulking for shipbuilding and essentially lived on his own, paying for his own food and lodging, while sending the majority of his pay back to his owner.
Ultimately, of course, he escaped, becoming a major figure in the abolitionist movement, and renowned for his oratory. One of the great details is that one of the books he used to learn to read was a book of famous speeches, and he apparently absorbed it, cover to cover. Some of the ancient Roman speeches regarding slavery inspired his own abolitionist thinking.
While occasionally bogged down in petty rivalries within the abolitionist movement, Douglass also had a broad scope and was one of the many people involved in both abolition and women's suffrage. This was a two-way door and many (white) women were also supportive of abolition. This didn't always go down well, or be reported fairly:
"the tenth-anniversary meeting of the American Anti-Slavery Society was moved after being barred from the Broadway Tabernacle), reporters took salacious note of what they chose to see as the 'semi-flirtations' in a meeting 'chiefly composed of members of the fair sex,' but attended as well by 'sable-complexioned sons of Africa'"
"On August 26, 1842, when [Abby] Kelley began her address to an antislavery convention in Rochester, in the Third Presbyterian Church, the minister was so appalled that a woman was speaking publicaly, and ordered the small gathering out of the building."
In 1860, after Lincoln's election, things were clearly pretty hot. This Winslow Homer print gives an idea of the brawl that occurred when a commemoration of John Brown was gatecrashed by members of the Constitutional Union Party. They were against secession, but not anti-slavery.
After the war, Douglass was far too optimistic about how ex-slaves and black people would just enter society. He seemed to think abolition and the vote would cure everything. I don't know that he had much experience of the Deep South, but that slowly dawned on him as lynching became common. Also, I think he may have underestimated his own genius and success. There is a whiff of that Bill Cosby tone of, if you all just got off your lazy butts, you'd be as successful as I am. I think he should have learned faster from the varied fortunes of his children, who with many advantages and riding his coattails, were always something of a disappointment to him.
Another poor choice was getting involved in the Freedman's Bank, which failed not long after he joined its board and lent his popularity to it. "Some scholars claim that the failure of the Freedman's Bank and the loss of their savings led to a distrust of all banking institutions for several generations among the black community."
Getting back to being out of touch. "Those with their eyes open to the oppression of black laborers in Mississippi and Louisiana in 1879 saw Douglass as simply wrong when he claimed that "the conditions … in the Southern States are steadily improving." His prediction "that the colored man there will ultimately realize the fullest measure of liberty and equality" was cold comfort in 1879."
His ambassadorship to Haiti was also somewhat mixed, although he seems to have done well when faced with some autocratic rulers and undiplomatic US military, who wanted a naval base there. Later he helped put on the Haitian pavilion at the Columbian Exposition in Chicago. Though there was kind of a shameful scene when the expo held a Colored People's Day and stocked up on watermelon. Many blacks boycotted it, but Douglass apparently took the opportunity to give a corker of a speech.
"The introductions over, Douglass rose once more, put on his glasses and began somberly reading a paper, "THe Race Problem in America." Suddenly he was interrupted by 'jeers and catcalls' from white men in the rear of the crowd. In the August heat, the old man tried to go on, but the mocking persisted; his hand shook. Painfully, Dunbar witnessed his idol's persecution; the great orator's voice 'faltered.' Then, to the young poet's surprise and delight, the old abolitionist threw his papers down, parked his glasses on them, and eyes flashing, pushed his hand through his great mane of white hair. Then he spoke: 'Full, rich and deep came the sonorous tones, compelling attention, drowning out the catcalls as an organ would a penny whistle.' 'Men talk of the Negro Problem,' Douglass roared. 'There is no Negro Problem. The problem is whether the American people have loyalty enough, honor enough, patriotism enough, to live up to their own Constitution.'"