Once again, go visit a tax professional who can provide you with some advice.
There are three areas that need to be addressed as to whether or not the costs you are referring to are a repair which can be immediately expensed or must be capitalized and depreciated.
A capital improvement is defined as an amount paid after a property is placed in service that results in a betterment, adaptation, or restoration to the unit of property or building system.
Are you just re-shingling? If the answer is yes, then that is most likely not a betterment or restoration. If you are replacing 20 year shingles with 50 year shingles? That would be classified as a betterment. If essentially the same type of shingles, than that is not a betterment.
How much of each roof layer was replaced? If only the outer roof covering (membrane, shingles, etc.) was replaced but none of the underlying roof system, it is not a restoration. If any load-bearing structural elements (including decking and sheathing) were replaced that supported more than 40% of the roof, the entire cost is likely a restoration. If more than 40% of the insulation layer between the roof covering and structural elements was replaced, it may be a restoration.
As you can see, there are many factors in deciding whether or not this is an expense (repair / maintenance) or must be capitalized.
*A reminder that posts in a forum such as this do not constitute tax advice.
Also keep in mind the date of replies, as tax law changes.
