So, it's tax season, and I could use some help. I thought I'd be able to tackle my taxes on my own, but I'm worried that's not going to be the case as I learn more about how complex they can be. However, for a variety of reasons, I'm still hoping to understand some specific things about my tax situation a little more, if possible, just to have info for when they're prepared, or worst case if I have to try and attempt them myself since it's already close to the filing deadline.

Here's some detail about my situation. I bought a property in 2020 to fix up and rent. It took forever, and I finally finished early 2024. I know, I know. It's been rented out as a month to month rental since approximately May between 2 separate renters. I've spent the time compiling all the material and labor costs that accumulated throughout the years of renovation to determine my cost basis, however, I wasn't sure how to write off the years of insurance and taxes that I paid but never wrote off because the property wasn't rent ready yet, or if that's even possible since that's even possible.

Looking at my tax burden as a whole, I earned rent income as well as investment income, totaling only around 28,000 (14k from rent and 14k from stock investment profits taken). My deductions from the rental, without anything added related to my question about past years taxes/insurance, comes to approximately 21k (this includes things like vehicle insurance, too, which is something I'm not sure if I can deduct). Related to this, I have another property that I've been renovating since finishing the last one and it's almost complete that I've paid insurance and taxes on.

So, my main questions are (while using a 1040 schedule E):

1. Can I add together and deduct the insurance/taxes from 2020, 2021, 2022 and 2023 on my 2024 taxes from the first property?

2. Can my deduction from the rental be applied to the capital gains from my stocks since the losses greatly exceed the income from just the rental in 2024?

3. If the answer to question 2 is yes, should I/ can I, apply the tax/insurance payments in 2024 on my second property toward my overall taxable income from 2024, or should I wait and take that deduction in 2025 when it's complete and starts generating rental income?

Thanks in advance for any help, and please feel free to add anything I'm likely missing.

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Tax questions about 1040 Schedule E rental property

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