Isn't the safe harbor only $500 in his case? If he wants to deduct the whole thing currently he would need to prove its a repair and not an improvement. An improvement is defined as a betterment, adaptation, or restoration:
1. An expenditure is for a betterment if it:
ameliorates a “material condition or defect” in the property that existed before it was acquired or when it was produced--it makes no difference whether or not you were aware of the defect when you acquired the unit of property,
results in a “material addition” to the property--for example, physically enlarges, expands, or extends it, or
results in a “material increase” in the property's capacity, productivity, strength, or quality.
2. An expenditure is for a restoration if it:
returns a property that has fallen into disrepair to its “ordinarily efficient operating condition”
rebuilds the property to a like-new condition after the end of its economic useful life, or
replaces a major component or substantial structural part of the property
replaces a component of a property for which the owner has taken a loss, or
repairs damage to a property for which the owner has taken a basis adjustment for a casualty loss.
3. You must also depreciate amounts you spend to adapt property to a new or different use. A use is “new or different” if it is not consistent with your “intended ordinary use” of the property when you originally placed it into service