I use Turbo Tax. It is inexpensive (@ $50) and it steps you through the various quesitons. I do not think you can write off your roof. The exception would've been if you had taken a Home Equity loan, then you can write off the interest of that loan.
I found this on irs.gov
Table 3. Adjusted Basis
This table lists examples of some items that generally will increase or decrease your basis in your home. It is not intended to be all-inclusive.
Increases to Basis Decreases to Basis
Improvements:
Putting an addition on your home
Replacing an entire roof
Paving your driveway
Installing central air conditioning
Rewiring your home
Assessments for local improvements
(see Assessments for local benefits, under What You Can and Cannot Deduct)
Amounts spent to restore damaged property
Insurance or other reimbursement for casualty losses
Deductible casualty loss not covered by insurance
Payments received for easement or right-of-way granted
Depreciation allowed or allowable if home is used for business or rental purposes
Value of subsidy for energy conservation measure excluded from income
Improvements. An improvement materially adds to the value of your home, considerably prolongs its useful life, or adapts it to new uses. You must add the cost of any improvements to the basis of your home. You cannot deduct these costs.
Improvements include putting a recreation room in your unfinished basement, adding another bathroom or bedroom, putting up a fence, putting in new plumbing or wiring, installing a new roof, and paving your driveway.
Amount added to basis. The amount you add to your basis for improvements is your actual cost. This includes all costs for material and labor, except your own labor, and all expenses related to the improvement. For example, if you had your lot surveyed to put up a fence, the cost of the survey is a part of the cost of the fence.
You also must add to your basis state and local assessments for improvements such as streets and sidewalks if they increase the value of the property. These assessments are discussed earlier under Real Estate Taxes .
Repairs versus improvements. A repair keeps your home in an ordinary, efficient operating condition. It does not add to the value of your home or prolong its life. Repairs include repainting your home inside or outside, fixing your gutters or floors, fixing leaks or plastering, and replacing broken window panes. You cannot deduct repair costs and generally cannot add them to the basis of your home.
However, repairs that are done as part of an extensive remodeling or restoration of your home are considered improvements. You add them to the basis of your home.
Records to keep. You can use Table 4 (at the end of the publication) as a guide to help you keep track of improvements to your home. Also see Keeping Records , later.