Seconding the The Anarchist FAQ a very large and very comprehensive guide which is easy to navigate and will provide responses to the most common criticisms and ideas of anarchy
For beginners secondary sources I would recommend:
The anarchists by James Joll
Anarchism by George Woodcock.
These books will give you a nice overview of the different schools of thought and trends within anarchism and their arguments.
For a good overview of anarchist history in practice:
Demanding the impossible: a history of anarchism by Peter Marshall
As for primary sources start with
Anarchism - Errico Maletesta
ABC of Anarchism
+ If you want to see a the text that triggers the most people about anarchism and within anarchism here is catechism of a revolutionary by Nachayev
For basic arguments against it try
Left Communism and Infantile disorder by Lenin
Anarchism: A Marxist Criticism by John Molyneux
Honestly though just read one of the first two overview books and if any particular school, event or individual interests you go on from there, because yeah you can go through the whole movement chronologically starting from pusedo anarchists Christians all the way up to modern groups like crimethinc but chances are youll just burn out and not have a good time.