We are getting close to amounts where our income might be too high for ROTHS (Have to check this after the standard deduction.

The longer you hold the more amortized these costs can become while concurrently getting the help from appreciation, tax deductions, and principal pay down. 

@Ryan ProffitYou may or may not be required to provide her a 1099-INT.Not everyone is required to do so.Interest income is subject to federal and state income taxes.If her only other income is social security, standard deduction may be enough to wipe out all her taxable income.I know the person is a family member, but be wary on providing tax advice as you may not know everything about her taxes.

In many cases charitable contributions can be tax deductible.

There are also almost $3,800 in back taxes but my purchase contract states that all debts against the property will be deducted from the purchase price.

Can anyone recommend a service to automatically deduct tenant rent in Canada.

Make sure you send a certified letter and such with the deductions as your state requires.

Do I deduct the total original cost of the roof ($7,000)?

See article below.https://www.buildium.com/blog/tax-deductions-property-managers-2014/

Specifically, tax incentives/ deductions?