I am self employed and run a trucking company so I write off my income to pay as little tax as possible.

Definitely worth chatting with a tax pro to make sure you're set up in the best way possible.

How many of you have got your tax bill for this year?

Is this property tax deductible? 

Put it on the market, take your (up to) $500k tax free gain and buy a no attachment rental if you want.

My current flow is 1) find a house that matches the configuration (X beds, Y bath)  in a certain neighborhood (Redfin or my agent)2) pull up rent data in rentometer / Zillow 3) run through my spreadsheet with expenses, taxes, insurances and etc I would love these to be automated.

But since the rentals are on my tax returns, of course it's factored in when getting a new loan. 

One rule helped here (I simplify a lot): you should always count how much money will be left in your pocket after all expenses (including mortgage payments, taxes, fees, utilities, as well as the reserve fund for the current repairs of the property).

I'm attempting to help out a friend's parents who are about to lose their home to back taxes.Is the process as simple as quit claiming the deed to me and then I pay the taxes and hold the property until they pay me back?

Sure you have expenses and income tax, but still.......?