You have to separate maintenance from improvements. Improvements extend the useful working life of the property or add value; maintenance keeps the property in as-was condition. Roof and hot water heater are improvements.
If this is rental property and you are reporting the rental income on schedule E, you would include the cost of special assessments for building improvements as costs for improvements that must be depreciated over 27.5 years. Maintenance costs may be deducted in the year paid.
If this is your personal residence, these costs are not deductible. Improvements add to your cost basis and may reduce your taxable capital gains when you sell. Maintenance is just stuff you pay for as a homeowner and is never deductible.
