Is the right of way for a private road, leading to other properties? I would think that whoever is being affected by the narrowing of the road would be in the best position to pursue this.
I'm no lawyer, but I'd be skeptical that the entire HOA could be held liable for an issue that would occur on this one individuals property. Especially if there have been documented efforts to improve the roadway by the other owners. Further, even if the HOA is liable, that doesn't mean that all the other property owners are individually liable. So I wonder how much each individual actually has to lose? Worth consulting with a lawyer on that framework.
But if this road leads to someone's property, and then someone installed fencing that encroached on the 40 foot that is allowed for maintenance, I would think they would be in their rights to move the fencing to the edge of the ROW and perform improvements as they are needed. If it was my right of way, I might have a survey performed, then send a letter to homeowner to move the fence, then have it moved myself if nothing is done, and perform maintenance as needed. That is a separate issue from trying to collect HOA dues. Different problems.
As an aside, I find it a bit curious that a judge would continually rule against written contracts - unless they are poorly done. And as has been suggested, that decision could be appealed. Now, is it worth the legal costs for the bit of money you might be able to force out? Different question.
All that said, a legal outlet is often the worst way to deal with things like this. No one wins.