You can tag/categorize once a month to keep organized so at year-end all you need to do is turn in an exported schedule E report to your CPA. quickbooks requires alot more training and is not intuitive to setup for rentals and doesnt have the functionality built out of the box like quicken.

It's not worth the time or headaches dealing with "trained tenants" who don't want to pay rent.3).

I thought it would go a lot smoother then it did of course, but never would have expected the painter I hired through a personal training client of mine's referral, to just stop showing up and lose complete contact with for over 2+ weeks.

@Khadijah HolleyI would start with the known brokerages, they typically have training programs and mentors.  

They get trained quick or they have to leave.

@Kahla Henry there are probably several guru training programs that come though your city all the time.

I have been to guru courses and paid seminars and expensive year-long trainings.  

Assume your first few deals will be for training rather than to make a killing.

There is a large capital investment in training people for this work as it isn't something people can go to school for or that there are clear training programs for.

Pick a random S corp client of yours, be a robot, fill this out, you might be surprised:https://new-content.mortgageinsurance.genworth.com/documents/calculators/Training%20Form%2091%20(2017-2018)_12413401.pdfWe see people show up in a corvette, business bank accounts show $50k/mo coming in with only $5k/mo going out in expenses, then you fill out the form based on tax returns, and Fannie/Freddie think the dude is broke as a joke.