They told me new tenants should push out the very first payment manually and turn on auto draft for the next month.

You could auto sequence 100 at a time to go out at a scheduled date, but 100 would be the minimum.  

Stessa has an iOS and Android app that has a built-in scanner and auto-categorization feature.

Use rent collection software - most of them have ACH "pull"/auto withdrawal available.If the tenant wants to wire money that may cost you on your side.Don't allow tenant to control the conversation.Give two options:- here is the account info and bank - they can walk the cash or deposit to your bank and deposit it- ACH/auto withdrawal.That's it.

It turns out that the teenager is underage and thus the father's auto insurance is not going to cover it since the teenager wasn't on the policy.  

Hi, got another storyTenant signed 1 year lease with lease auto renew for additional 1 year if tenant does not give 30 day notice. 3 years later I get a text saying they will be moving in 3 to 4 weeks and last month rent can only be used the 11th month of lease expiring and move out. 

You could come at this kind of sideways.Find places that have the services and busineses that "income challenged" (RENTERS) like to use.Best would be if within walking distance, things like rent to own furniture, liquor stores, convenience stores, fast food - McD's Jack in the Box, 24 hour car parts, health clinics, (Bus Stops), buy here pay here car sales, a grocery store, Target, WalMart, auto repair shops, etc..Things they need and can afford.  

I suggest putting other things on hold like credit cards, student loans, auto loans, personal loans, stuff like that.

There are plenty of auto enthusiasts that would consider a ten year old BMW a POS.

Income goes direct to my bank account and I pay everything auto pay through my bank.