A question of sources
The problem is the issue of the source material. We're using works compiled by hobbits of the Shire, whose history and legitimacy resulted from a decision by a Numenorean monarch to allow them to settle there. There's also the Rohirrim, whose title to their lands resulted from the Oath of Eorl, a decision of the ruler of another Numenorean state.
The overwhelming amount of material we have is either Numenorean or at least pro-Numenorean. In terms of what you said here, Ivriniel:
I wonder if the Dunlendings were expected to pay taxes to Gondor and Arnor for example, during -- as Dunlendings would have put it -- "the occupation".
Dunlendings were antagonistic to Rohan and Dunedain and the conflict emphasised jealousies and conflict over sovereignty of the region.
You may be right; but I don't think there's enough material to enable us to conclusively judge.
In terms of what might be done to settle the matter after the War of the Ring, we read what King Elessar did on 4 occasions. He granted the lands around Lake Núrnen in Mordor to the slaves who farmed them, whom he freed, although we don't know if they formed an independent state or states. He let the Drúedain be, declaring that none may enter their woods without their leave, which appears to be a recognition of their independence. Regarding the Shire, he declared that it was a free land under his protection, and forbade men to settle there. It appears, although it wasn't explicitly stated, that he did something similar to Bree. He certainly appears to have let it alone.
Perhaps the Dunlendings or other folk might have approached Eomer or Elessar, making offers of accepting their overlordship in return of an amount of autonomy, referring to what was done to the Shire and Bree as precedents?
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