Knowing that AI has natural language processing skills, I was hoping to see if it's possible to point, teach, interact, and then pull back responses for prospecting purposes.

Quote from @Jr Miller: The lack of human interaction increases our number of showings.

Plus, Zillow, Rentler and the other real estate platforms tend to have all sorts of unnecessary hoops to jump through for landlords, and I find a lot of their design very un-intuitive (I remember spending waaayyy too much time just trying to figure out simple things in Rentler).  ...why can't they make it easier?

My recommendation is to first learn in detail how the foreclosure process works in your state then you may be able to intuit how lenders strategize selling the properties. 

This is a touchy subject.If you observed specific concerning behaviors during interactions, such as rudeness, aggression, or disrespect for property, these could potentially be valid reasons for rejection if documented properly.You should add one very important things to do on your checklist, past landlord references and it must be legit and find out why they aren't there any longer.

Every interaction with them has raised red flags. 

The number one problem with RentRedi is the total lack of customer support and yes with Intuit you will have to talk to an oversees call center but every question I needed help with got answered and all problems got resolved.

By being physically present, you can gain valuable insights into the property's operations, interact with residents, and assess the team's performance.

Of course, after that brief interaction, I'm pretty sure I just become lost in a sea of other text messages.My question is do any of you see a way to utilize a strategy like this?  

I ended up deciding to use TSheets from Intuit https://www.tsheets.com/- it is working well for me!