A new federal law levies specific requirements on all association boards with some heavy fines; you can search "Corporate Transparency Act" or read my article on that here.   

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.

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.