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A recommendation by a vet who sees the dog, your own investigations and the fact that the dog licks and chews at the tail would be enough to convince me to have him redocked.
As far as why his tail looked OK at a year and is now a problem could be for a number reasons--neuromas sometimes develop over time and there is some bone growth on the vertebrae even at year. If you are concerned that your vet may not have correctly diagnosed the problem ask for a consult with a vet neurologist as well.
And your dog looks to have enough tail length that his redock probably won't be as short as the average Euro type dock. In redocks what is generally done is that as much skin is saved as possible and bone and neural tissue removed, then the skin is pulled back over the stump so that there isn't pressure on the bone--many of these kinds of problems start because the tail was originally docked through a vertebrae not between two vertebrae--even experienced docker can have this happen because it can be tough to feel and dock between the vertebrae.
You may find that old, ingrained habits die hard and you'll have to initially teach your dog to leave his tail alone.
Good luck and I'd definitely redock in this particular case.
Last edited by dobebug; 06-20-2017 at 08:57 AM.
Reason: A million typos