The following is based on the chronology of the Age of the Solar Clipper
There is a prequel titled Dark Knight Station. It introduces some characters that are main supporting caste throughout.
I don’t know that I would actually read this first. It fills out the background on some good guys and a major villian that shows up later.
The main series starts with this title and introduces two of the main characters. This is not a military space opera series but I enjoyed it immensely despite that.
The following books include Half Share, Full Share, Double Share, Captains Share, and Owners Share. They all track the career advancement of the main character Ishmael Horatio Wong.
This is where the chronology goes a bit strange.
A spinoff trilogy that starts with Milk Run introduces a separate story line with a different two main characters. All of the events occur between Double Share and Captains Share in the main series.
The second spinoff trilogy that starts with In Ashes Born follows immediate after Owner’s share in the main series. This is where the two main characters from Quarterr Share join back up and the final book in the this trilogy does a nice job of rolling in the two main characters from the other trilogy in the final book.
I did have an initial problem with Milk Run. When I first listened to Milk Run, I quit after the first couple of chapters. This was in part because the narrator doesn’t lend herself well to a 1.1 speed setting. The other problem was that I found the start to be a bit stupid. Once I decided to give it another shot and got through the first five (short) chapters, the story got really good.
I’ve listened to all of these books many many times and know I will enjoy them many more. The one caveat is that I skip to chapter six on Milk Run now that I’ve read the setup for the story once.