It may not be here tomorrow, and taxes won't matter then.That said, if you're trying to estimate your future tax benefits, keep in mind these things:- depreciation is only applicable to rentals- depreciation starts when you place the property "in service," not when you buy it- depreciation increases your deductions and consequently your tax losses, but you may or may not be able to benefit from these losses, depending on your overall tax situation- if you do have room for additional depreciation, you may be able to amplify it with cost segregation (a separate topic) 

It does NOT mean that if you buy a Safeharbor 401k document that you're "safe" from severe IRS & DOL penalties if the plan is not operated compliantly.From a plan design perspective, "Safe Harbor 401k" is often NOT the optimal design and results in unnecessary costs to the business owner AND missed tax deductions.

They also take too long to pay their invoices, and on top of that they deduct 10% from the payment to us for "commission". 

And if you hire a property manager, deduct another 10-12%.I think this property could work if you are careful to set aside the cash flow and build a solid reserve.

And then when you say gross $85k, I'm deducting all expenses for mgmt, PITI, utilities, etc. and coming up with a net (for example $30k leftover). 

If you don't have income, the IRS will probably catch up with you on filing tax returns for a business with deductions but zero income.However, if you don't care about your corporate veil and don't care about claiming your expenses as deductions (remember, nothing says you have to...), then go ahead --- is my layman's opinion. 

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.