You can summarize your transactions yearly by SchE tax category to support tax filings.Hope that helps. 

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.

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.

You should consult with your local housing authority.

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?

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 am working a deal to help a developer acquire a tract of land in Charlotte County, Florida. The problem is the county is wanting to charge $15,000 per unit, which would come out 2.5x the amount he is paying for the ...