Takiro
Well here is what we know from canon information. The map of the Free Worlds League after the Age of War (2571) shows worlds colonized at that time. The Duchy of Tamarind includes six worlds in 3025 but Hell's Paradise, Promised Land, Millungera, Saltillo, and Kosciusko are not colonized as of 2571. In 2452 Bella and Alula Australis (I tend to believe this is Alula Borealis) taken by Peter Marik from Lyrans indicating they belonged to the Commonwealth.
So here is what I propose; the Bolan Association was a nine world proto-state originally consisting of Bolan, Valloire, Marsalle, Kamenz, Rochers, Dixie, Ilion, Nockatunga, and Tamarind. This free trade union assembled in the wake of the Outer Reaches Rebellion (2242) allowed its member worlds to survive and indeed thrive in a post Terran Alliance Human Sphere.
Philosophical Views; perhaps the finest merchants in Marik space
Question; when does the Association join the FWL? Would it be prior to 2293 which is the start of the Stewart War or after the Lyran Commonwealth was formed in 2341? The HBHS map shows the Protectorate of Doegal 3-4 jumps away from Bolan space. It might take Steiner 20 years to at least “threaten†the Association.
The Association endured significant damage during the Age of War with many of its worlds being assaulted in one form or another. The strategic location of the Bolan Thumb was too big to pass up during the Age of War.
Wealth and opulence during the Star League era as peace with the Lyrans bought prosperity and growth to the Association. Swelling to almost two dozen worlds (23) it becomes the fourth largest province in the League. Not quite as big as the Big Three but the Association would double the next largest province. As such would Bolan as a region be more loyal to the Star League than the Free Worlds League? Especially to someone like Kenyon?
Question what is their reaction to the Scourge and the fall of the Regulans? Do they try to ascend to the next level and become one of the big 3? Do they assume the Regulan role of opposition or do the Mariks identify them as a potential threat?
What was their role in the Marik Civil War? If neutral could their lack of commitment be considered a worse then choosing a side?
What is their current role? Was the fall of Bolan a plot by the government? Were they part of the opposition?
How do you like all of this?