I got captcha a couple of times at the start, but then it stopped. Forgot to count how many ....

Below is her Janeness' list of Alliance/Union books in chronological reading order, not published order. Though this was requested elsewhere, I'm creating it as its own topic so it's easier to find. Enjoy!

Events leading up to the First Company War: Hinder Stars
Alliance Rising

Events leading up to the Second Company War: Sol System
Heavy Time 
Hellburner

End of the second war:
Downbelow Station

Sol Post War: Sol's expansion toward Ursa Major stars rather than Barnard's (Tau Ceti)
The Pride of Chanur 
Chanur's Venture 
The Kif Strike Back 
Chanur's Homecoming 
Chanur's Legacy

Union Post War: 
Forty Thousand in Gehenna 
Cyteen (Also published in three pb volumes: The Betrayal,The Rebirth, The Vindication)
Regenesis

Alliance Post War:
Merchanter's Luck 
Rimrunners 
Tripoint 
Finity's End

Way down the timeline, loosely related, if you squint

Brothers of Earth 
Hunter of Worlds 
Serpent's Reach

Faded Sun: Kesrith 
Faded Sun: Shon'Jir 
Faded Sun: Kutath

Morgaine Books
Gate of Ivrel 
Well of Shiuan 
Fires of Azeroth 
Exile's Gate

Rider at the Gate 
Cloud's Rider

Port Eternity 
Voyager in Night 
Cuckoo's Egg 
Hammerfall 
Forge of Heaven