I haven’t paid taxes since I bought them due to deductions such as depreciation and interest payments.

What is a reasonable way to apply an estimated tax benefit of the interest deduction vs. the tax on increased positive cash flow vs. invested income? 

I am looking at my first rental property investment, with the current rates and San Diego pricing cashflow is very hard, so I wonder if I should remove tax property and insurance from my cashflow calculations as they are 100% deductible at some point.

Your cost to attend court is a tax deductible expense but I don't believe it is something that can be added for the judgement.

@Frank ChinBased on the opportunity value of cash your equity, if your mortgage free, is most likely creating negative cash flow from your investment property.With the opportunity value of cash at a minimum of 10% for every 100K in equity you must deduct $833/month from your rental income to insure a accurate accounting of your TRUE income.Investors must keep in mind every property has two separate income generating streams.

That seems to be the opposite of what everyone is telling me here.I will have very little capital gain after deducting my points and closing costs on this home that I purchased less than one year ago.  

But one good thing about keeping it as an STR it qualifies you as RE professional and would be able to deduct from your W2 income.LTR is much more hands off especially if it is a new build.

You get to deduct 3.3% of the value of each property off your taxes each year (in addition to all the other expenses).  

My medical is $528 a month for a family of four (1-year plan, high deductible, $1M coverage per person) Like with most policies you get a discount, if you pay in full.

I specifically excluded *bonus* from that prior post for that very reason of ineligibility, however, if the cost seg carves out 20% of the basis as 5-year, 20% as 7-yr, 20% as 15-year and the remainder as 39 year (assuming commercial), that’d still front one heck of a depreciation deduction using MACRS 200% DDB.Will still be some net gain, but that would dramatically dramatically reduce the cash he’d have to fork out to uncle sam… PLUS … he’d have new depreciation again!