And my wife and I made an automated $25 contribution monthly to each of their account.  

For example, if you are going to require them to pay rent via an automated system, explain that clearly and give your reasons. 

Our CRM is highly automated on the sales side.

Is this one of the softwares to automate things that I should be using more of? 

Additionally, there are some tools available to you where you can bring a certain level of automation to that rental management process (ie. automatically syndicating a single listing to 10+ major listing sites, thorough tenant screening with full background checks, digital lease creation, automated online rent collection, and maintenance tracking).

I specifically with work in the area of automation and have found the articles by Aaron Kinney who focuses on automating his real estate business to be great sources on how to scale up.https://www.biggerpockets.com/renewsblog/author/aaronkinney/

I am working on building a automated company whole selling real estate.

My goals is to do 100 deals a year, what tools, software, and technology can I use to increase my real estate investing business, and automate the business to do more deals and maximize time!

If you could self manage by automating your checkin with a smart lock then you could improve your numbers drastically.Also you keep mentioning tax free.

I would rather automate other parts of my job to free up time for interviews to save myself the headache of dealing with idiots.Hope that helps!