The siding and roofing you installed on your rental property are considered as capital improvements and the expense is not deductible.  The cost of a capital improvement is added to the adjusted cost basis of your rental property and is not deducted as an expense on your tax return.  A capital improvement is the addition of a permanent structural change or the restoration of some aspect of a property that will either enhance the property's overall value, increase its useful life or adapt it to new uses.

Where  do I enter the cost of a new roof on a rental property

Your new roof and siding add to the cost basis of the property. It gets entered in the Assets/Depreciation section. You should classify the improvement as Residential Rental Real Estate. Enter it's cost in the COST box and enter a ZERO in the COST OF LAND box.

THe cost will include everything - what you paid for it, cost of installation, transportation, absolutely *EVERYTHING* associated with the property improvement. That total cost gets depreciated over the next 27.5 years.

In service date is the day after the work was completed, and the business use percentage is ONE HUNDRED PERCENT business use.