William S. Lind composed the Canon to provide readers with a solid understanding of the intellectual foundations of maneuver warfare.   (Disclaimer: I am the author of one of these books.)
Mr. Lind recommends that the books of the Canon be read in the following order, which reflects his ‘generations of modern war’ theory.
Charles Edward White, The Enlightened Soldier
Robert Doughty, Seeds of Disaster*
Bruce Gudmundsson, Storm Troop Tactics*
Martin Samuels, Command or Control
Robert Doughty, The Breaking Point*
Martin Van Creveld, Fighting Power*
Those who prefer a strictly chronological sequence may want to read the books in a slightly different order.
Charles Edward White, The Enlightened Soldier
Bruce Gudmundsson, Storm Troop Tactics*
Martin Samuels, Command or Control
Robert Doughty, Seeds of Disaster*
Robert Doughty, The Breaking Point*
Martin Van Creveld, Fighting Power*
This alternative sequence offers readers the additional benefit of allowing readers to engage the Seeds of Disaster and The Breaking Point as a single unit. Â (The Breaking Point was written as a sequel to the Seeds of Disaster. Â Thus, many of the individuals, ideas, and institutions described in the first book appear in the second.)
A third approach would be to read the series in reverse chronological order, starting with Fighting Power and ending with The Enlightened Soldier.  This ‘backwards’ sequence has the advantage of starting with an event (the Second World War) that is familiar to many present-day military professionals before moving on to times and places that are less well-known. Reading the Canon in reverse chronological order also puts the most difficult book to read at the very end of the series, thereby giving readers a chance to get their reading muscles in shape before they tackle the intellectual equivalent of a marathon.
The books marked with an asterisk (*) can be readily obtained, whether as trade paperbacks or e-books, at a reasonable price.  The other books, however, are much harder to find.  Thus, members of a reading group that wants to study the Canon in full may have to resort to such expedients as inter-library loan and placing books ‘on reserve’ in the duty shack.
The author of The Enlightened Soldier is currently writing a multi-volume biography of Gerhard von Scharnhorst. The first volume, new copies of which can be had for less than half of the cost of a used copy of The Enlightened Soldier, emerged from the press three years ago. (I recommend buying directly from the publisher, which will reward your defiance of the Borg with a 30% discount.)
Readers wishing to take a deep dive into the ‘education of the Enlightened Soldier’ may want to read the article of the same name which was published in the Marine Corps University Journal in 2018.
Readers who enjoyed Command or Control will want to read the sequel that came out in 2019. Called Piercing the Fog of War, it can be downloaded (for free) from Academia.edu