Exactly what @Bruce Lynn said, no one should be relying on anything automated when it comes to true market value. 

Send automated email remainders and late rate3.

What are the best ways to automate collecting rent from tenants that is on automatic payment and sends notification to tenants that rent is due?

Mainly, the systems implemented are fascinating (VA, automated offers, etc.)

As long as you do one thing at a time until it is fully automated, you should be good! 

Called the dude, and he had some weird automated answering service asking if I'm interested in selling.

They have automated systems such as an online portal for tenant requests for main/repair and the tenants also have different options to make the monthly payments online.

Also, remember that it's free to utilize a real estate agent to check out some properties, hear their insights and have them set you up with automated emails that will alert you when a property goes on the market that meets your criteria! 

- How best to automate monthly rent payments?

Of course for some homes it does not make sense, we are very direct about that.In addition, there are also automated modeling platform options on the market, our sister firm offers and option at  www.DIYcostseg.com, which utilizes our database history of over 14K fully engineered studies.