The negotiations between the town of Wellfleet and the Chequessett Yacht and Country Club over mitigation for the flooding expected to result from the Herring River Restoration Project were at times contentious. A Provincetown Independent newspaper article reported on deliberations during a January 6, 2021, meeting of the Wellfleet select board:

Helen Miranda Wilson told fellow select board members that the Herring River technical team had "bent over backwards for many years to look at all the details in good faith to make this happen with the club." Wilson added that the club "is trying to pull the rug out at the last minute." The select board voted to give the country club until Jan. 29 to reach an agreement with the Herring River team, or else the town would move forward without one.

A month later (on February 9) the Wellfleet Select Board unanimously approved an agreement between the town and the club that would allocate $6.7 million for flood mitigation. According to the budget, $5,057,192 will be used to elevate five low-lying tees, fairways, greens, roughs, and sand traps that would be flooded by the tidal restoration. The remainder of the $6.7 million ($975,000) will compensate the club for loss of business during the estimated two years of construction.

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