We have been working diligently at transitioning all tenants into the 21st century with ACH payments and using an online portal for maintenance requests.

Have you considered an online payment portal for your tenants?

Their website, communication, and online portals are usually garbage, and when I have 40 documents to submit each closing, it drives me up a wall to send 100 emails back and forth.

Most courthouses have portals for public use to assist in locating the filings.

I take their card number right over the phone and..most of my tenants dont understand payment portals or want to deal with them...

I have a lender or two that will ask for appraisal funds up front, but this  is done through a secured portal and it is disclosed that the funds are refundable should your deal fall through before an appraisal inspection is performed. 

My first goal would be to automate a majority of the processes such as lock codes, online portal to schedule visits, tours & payments, submit questions.

You just have to do your due diligence to vet the tenants.https://www.huduser.gov/portal...

I switched to a local bank and use their online portal to set it up.

Have you considered looking at Title III projects with licensed Portals instead?