I have used a totally new account on a new IP address at starbucks, with new text, new pics, new EVERYTHING, not even using a phone number, and I've had ads auto flagged.

The house hasn't been rehabbed in 30-40 years so the condition of the plumbing, electrical, and mechanical behind walls were unknown. 

Also, I feel I need to get a CRM with and auto-responder. 

Great questions - I too want to understand these "low level mechanics" of Sub2's.  

We set them up on ACH auto banking for their rent, we show them how to log into their portal to place maint requests, we also explain how our eviction process works and what will happen if they do not pay. 

What you will need off the back is an website which if you don't have that then you will have a hard time automating the process.Next you will need an auto responder, seo, video marketing, online presence, blogging and a management tool.

I served from 1999 to 2003 as a jet mechanic (aviation machinist mate). 

A good business person in, say the auto parts business, may give you some general business knowledge, but you'll be totally green starting out in RE.

I knew that some of the mechanicals would need to be updated.

My lease also automatically renews so as long as neither of us (me or tenant) says anything it's all on auto pilot.