Sorry for the canon dump, but I was curious as to the events surrounding Maidenpool in our timeline (that is, between A Game of Thrones and A Clash of Kings). This is especially difficult because Maidenpool isn't mentioned at all in the first two books.
A Storm of Swords, Jaime.
Maidenpool is ruinous and deserted.
At Maidenpool, Lord Mooton’s red salmon still flew above the castle on its hill, but the town walls were deserted, the gates smashed, half
the homes and shops burned or plundered. They saw nothing living but a few feral dogs that went slinking away at the sound of their
approach. The pool from which the town took its name, where legend said that Florian the Fool had first glimpsed Jonquil bathing with her
sisters, was so choked with rotting corpses that the water had turned into a murky grey-green soup.
When did this happen? That is what I'm curious about. The following quotes leads us to believe it was sometime during the events of the War of the Five Kings.
A Feast for Crows, Brienne
"Lions sacked his town, then wolves, then sellswords, and his lordship just sat safe behind his walls."
“’Twas nearer Maidenpool, m’lady, but the wolves burned us out"
The lions (Lannisters) sacked the town first, but might not have burned it, but the wolves (northmen) definitely did. So,
When did the "lions" sack Maidenpool?
This could be when Tywin sent Gregor Clegane to wreak havoc on the Riverlands in the events of A Game of Thrones. We learn that Sherrer and Wendish Town were sacked by "lions" in Ch. 35 Eddard 9. If we decide this is when the town is sacked the first time, then it certainly happens before the setting of our server.
However,
It makes more sense if Tywin's army sacks the town after the
Battle under the walls of Riverrun when Tywin chases down all the lords of the Riverlands as they retreat. I should think it would take more than a small force like Clegane's to sack a walled town like Maidenpool. By chapter 56 of A Game of Thrones, Tywin has reached the crossroads and set up camp. The proximity of Darry to the crossroads would indicate that Tywin has already captured Darry.
Tywin retreats to Harrenhal by chapter 69.
It is reasonable to assume that between these two chapters, Tywin had captured Darry and sent forces to Maidenpool as the Lannisters would not have sacked Maidenpool after the order to retreat to Harrenhal was issued.
By chapter 7 of A Clash of Kings, Darry has been recaptured by Darry's men, and we can assume, by extension, that Maidenpool was sacked by the "wolves" around the same time, which follows the trend of the northern forces retaking the Riverlands systematically during the events following the
Battle of the Camps.
The Battle of the Camps happens very near to the end of A Game of Thrones, so I am willing to argue that Maidenpool was not sacked by wolves until the events of A Clash of Kings.
Conclusions
It would be difficult to come up with an explanation for how the "lions" might have sacked Maidenpool after the retreat to Harrenhal, especially considering that Robb's forces were retaking the riverlands shortly afterwards.
Canon suggests the Lannisters sacked, but did not burn Maidenpool. This makes sense as Tywin's forces were likely more restrained than Roose Bolton's northmen. Compare Tywin's relatively peaceful takeovers of several Riverlands castles to the Boltons burning of Darry in A Clash of Kings. Tywin's purpose for sacking Maidenpool was likely to take supplies for his army, and away from the Mooton's, neutering them, not to wantonly destroy the town like the "wolves" do.
Veggie do what you like with this information. It is
likely, but not certain, that Maidenpool has been sacked at least once at the time setting of our server.
What would choosing as sacked town do for the project? The gates are probably busted, the town ransacked and deserted (come to think of it, all of servers towns are deserted).
As
WhereRmyDragons pointed out on Discord, this could be a great opportunity for a unique build on the server, but it entirely depends on what you want to accomplish.