A lot of the data you are looking at in terms of what homes rent for down here are not accurate btw.

If the software is not simplifying your life or making you more accurate, you shouldn't use it.

But larger repair items such as appliances and mechanical, plumbing, electrical, roof windows doors etc should still fall under the landlord's responsibility.

You are required to file a complete and accurate return, which means reporting the income that you earned along with atleast the direct expenses that you incurred on your rental.There are two comflicting forces - Your tax accountant wants to be aggressive with deductions because it will entitle you to paying less taxes(now or in the future).Your lender wants to see as much income as that will increase your Debt to Income Ratio(DTI).The good thing is that you can speak with your lender about 'one time expenses', that were only incurred in that year and are not reoccuring. 

Make sure to shop around for the best rates and terms.Find the Right TenantsOnce you’ve purchased the property, screen tenants carefully to ensure you find responsible individuals who will pay rent on time and take care of the unit.

If there is no HOA because it has been family run, it will be dicey, but generally if it is a private road, all those on the road are collectively responsible for maintenance and improvements.

Allows you to get out of landlord responsibilities, and keeps a steady check coming in each month like rent does.

I seriously doubt it is a service animal, more likely a emotional support animal (a pet usually with papers off the internet)....I like Jonathan's description of ESA being handed out like cotton candy at a state fair...pretty accurate.

The key is to accurately reflect the type of income/expenses and the timing of everything.

So yes it can work, but you also need to be able to convert the responses you get into closing.