What do you mean by investment property?
If NOT a rental (you are simply holding it and hoping it will gain value) then the situation is complicated.
Prior to the TCJA of 2018, investors could choose to deduct investment costs as a miscellaneous itemized deduction subject to the 2% rule. However, this deduction was limited to the amount of actual investment income you reported as taxable income on the same tax return.
Or, investors could capitalize their costs. That means adding them to the cost basis. That does not result in an immediate tax deduction but reduces their capital gains when they sell. (For example, someone holding vacant land might choose to capitalize their annual property taxes instead of deducting them on schedule A.). To capitalize your costs, you must file by mail and attach a written statement of the costs.
After the TCJA, this is still up in the air. The code section says you can choose to capitalize costs that would have been deductible. Under the TCJA, the entire category of miscellaneous itemized deductions subject to the 2% rule is disallowed for 2018-2025. Since the costs are no longer deductible, they might no longer qualify for capitalization either. The IRS has not issues official guidance.
You may want to seek professional representation.
Finally and separately, any HOA special assessments for capital improvements (new roof, etc.) would be added to your cost basis. On a rental, they would be depreciated over 27.5 years instead of deducted. On a non-rental property, they would be added to the cost basis and would reduce your gains when you sell.
