Updated: Sep 25, 2019
I agree with Forbes there is nothing to really celebrate on April 15th or Tax Day. As Forbes points out April 15th should not be known as Tax Day, it is far from a holiday or memorable event.
April 15th is a dreaded a tax deadline. I do get personal satisfaction completing the return or filing a well-organized extension. An IRS compliance audit in 2012 improved my expense tracking and bookkeeping skills. After 10 long investigative days, the agent indicated his time was not well spent. On the last day, he said "It was not a profitable adventure for IRS. "
I consider myself lucky and the experience taught me so much. I learned how to use Quicken to categorize, better document expenses and successfully negotiate with the IRS. Most of all the IRS is nothing to fear. Each year the IRS has hundreds of changes to the tax code. The agents can not keep up with so many changes. Ultimately, each itemized expense has a unique interpretation. I lowered my initial tax liability from the audit by over 75% because I petitioned several expenses the agent told me were allowable for that year.
If you own rental property, your effort is focused on Schedule E Part 1. Which is the supplemental income and loss from rental real estate, royalties, partnerships, S corporations, estates, trusts, REMIC's, etc. Amazing the IRS can get that description at the top of the form.
Itemize rental expenses or depreciation expense with Quicken or Quickbooks....
A single income property is worth the investment of Quicken or Quickbooks. Either application can organize your expenses to the same line items on the Schedule E. Save yourself time and create categories in Quick or Quickbooks that are the same expense items 3-19 on Schedule E.
Here are two great YouTube videos for setting up categories in Quicken