I got into it initially to eliminate having to integrate my bank with Quickbooks but rather have both of those pieces together in one place.

Were looking for tenure (15+ years) - that right there eliminates 80%+ of the list....

You can do tenant screening, all numbers, ACH payments and host of other features. 

A lease to own approach will depend on how much Seller wants to cash out and eliminate the property liability.Good luck!

Any way to eliminate one or more of these manual steps?

The units won't have HVAC system due to the cooler climate but because of the tightness of the home i.e <3 ACH, I actually need an ERV so I don't kill my tenants due to C02 or VOC poisoning.The problem is ERV filters need to be replaced every 3 months for all 4 or 5 units.

We want to begin by house hacking with a duplex in order to eliminate our current rent payment and have more cash to invest. 

We manage 37 doors with that costs us a few dollars per door per month with no surcharge for ACH payments and we get next business day credit for those.  

I was thinking maybe we could set up a ACH auto withdrawal from her bank or unemployment card to ensure the rent, any thoughts or complications with that? 

Receiving government guaranteed rent every month is priceless and hugely eliminates risk for out-of-state and out-of-country investors.