Just deduct security deposit and move on.

Right now, the best offers around me are for some 1.3-4 million, that only generated around 100k per year gross, so there would be a high chance of not cash flowing, and paying money, especially with a commercial loan (these buildings have more than 4 units).I was thinking that although the rental itself does not generate money, I would be able to deduct the mortgage interest, and depreciation from my personal w2 income and would be net positive.

Bigger Pockets is a great place to find a real estate tax accountant.A good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant who specializes in real estate taxation, business taxation, financial planning and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.

You only want to file a claim if it's much greater than deductible or your rates shoot up pretty quickly. 

Unless you are itemizing your tax return, the interest on the primary is not tax deductible.

Deductible: This is not a coverage but rather your portion of a claim.

Well, three top reasons come to mind:It will allow you to deduct their earnings on your own tax return.It is required by law for any person to whom you paid at least $600 in 2023, total.

You’re paying $70k in “non-deductible” interest in exchange for less deductible interest. 

My main account has all the rents deposited and all expenses deducted such as mortgages, some utilities and an electronic payment app connected to the account to pay contractors.

If the cost of rehabbing it is more than it’s insured for, they’ll just cut me a check for what it’s insured for minus the $2,500 deductible.