I like the idea of the automated replies to save time.  

One lawyer might say its fine and one might say stay away from anything automated. 

Manufacturing jobs lost will not come back and AI, Automation and big changes to retail and logistics could eliminate many current jobs like Truck drivers.

I have received, from a combination of numbers, robo dialer calls from people claiming that they have driven by my properties and would love to talk about doing a deal. I also receive text messages to this effect.
My...

On average I'd say about 22-25% of my calls actually lead to another person on the line, not a voicemail or automated response.

You will need to find a broker that will manually underwrite your file and point out that she is your sister, automated underwriting will kick it out.

Start developing processes and automation applications to increase efficiency of handling my current RE investments o free up more time for research and making offers.

If you use one bank, when you log in, you should see all of your bank accounts for each property.In regards to rent collections, if you use a rent collection website like https://Avail.co (that's the one I use), you can specify the Bank Account where your rents are to be deposited.When it comes to paying expenses, all the City (Property Tax, Registration fees, etc.) and Utility expenses (Heating, Electrical, etc.) are automated on each of these County and Utility website.

So far the only way that I have been able to discover this is by calling up the town… but maybe there are websites and resources to automate the process a bit more?

I would recommend you don't average automated valuations from these sites.