Very Large Boat Garage

We have a new homeowner moving into our neighborhood who has informed us that he intends to build a 30 x 40 metal shed for his boat. He was given the covenants before he put an offer on the house, but is now claiming 'hardship' (He feels he should get a variance because he didn't fully understand the restrictions before buying the house.)
The structure breaks at least 3 covenants (incompatible materials, no front facing garages, detached structures) and the size is VERY large - it is equal in size to the footprint of the main house.
We are going to be forced to 'lawyer up' as a voluntary HOA (I am a former officer and on the architectural review committee). His proposed structure is going to be an eyesore and is completely inappropriate for the nature of our neighborhood.

My question: Would I stand a better chance of fighting him as an individual homeowner who's property value will be negatively impacted by this structure (BTW, we live next door), or should we fight this as an HOA? My understanding is that HOAs usually lose cases like this.

Allow me to clarify - the HOA officers are voluntary, as is the ARC.
Owner agreed to abide by the covenants when he purchased the house.

So the HOA is mandatory, but the board and ARC are all volunteers, that is very different than a voluntary HOA.

I agree with John. I'm not sure about TN, but in most places HOAs have a decent chance of prevailing with blatant covenant violations. Obviously without reading your docs, knowing TN case law, and researching the facts of this case, it is impossible to tell you what your chances are, a local attorney versed in HOA law should be able to give you a more accurate opinion.

As far as suing yourself for loss of value, that seems like an uphill battle. For starters, you wouldn't have any damages until you tried to sell, I don't know that suing for potential future damages is very likely to get you anything. Proving the amount of damages would also be challenging.

If you go to court you'd likely be looking for injunctive relief based on the violation of the covenants. That should be enough. Other considerations, such as property values, aren't going to matter. I think the chances of prevailing against the boat garage owner would be high (not a lawyer tho) as long as there aren't a bunch of other owners getting away with similar violations.

It is better for the HOA to simply enforce the CCR's. This is a contract agreed to at time of purchase and new owners have obligation to read and understand or ask an attorney if they do not understand BEFORE purchasing. Failure to perform due diligence does not later end up as a hardship.
If the HOA does not enforce and an owner sues, then best bet would be to name both the Owner and the HOA in your lawsuit as both are violating the contract.

As others suggested if the HOA attorney sends a letter noting the CCR violations and the fact he can be sued if violate, most likely the new owner will back down. The new owner if violates and builds anyway could end up in a lawsuit having to remove an expensive garage. Keep in mind IF this happens their could be certain statutes of limitation. For example in my state if the HOA does not file against someone violating in this manner within one year then the violator can keep his garage. In that scenario the HOA would loose the lawsuit if filed after one year.