I am unaware of any software that can automate this. 

Having a good mentor to help you navigate will influence the level of difficulty and how you maneuver so I think it’s highly important.

I am house hacking and doing my taxes right now (online with tax software).

Looking for advice on payment collection/managment software.

Certain tax softwares such as turbotax and the like have the functionality to electronically file.

But he told me that would be a waste of time and money because he is using the same software as I did.

It's wise to take into account market research and any upgrades or additional benefits for the tenant.Determining when to raise the rent is influenced by various factors such as lease renewal dates, local market conditions, tenant satisfaction, and lease agreements.

The bad news is that many influencers make it look much easier and give some false promises to get you to buy a course. 

To your question, I get leads with a prospection software or just walking up the streets and looking for signs of distress.

What is a simplistic software to assess current property as well as keep track of finances such as profit?