Montgomery is a nice size city.

When you're just starting out, your opinions are skewed because of  small sample size. 

some of the books you mention are great but are big picture idea books, and you may be thinking ...how do I select a place, inspect, buy and rent it (advertise, screen and select tenants, maintain it, etc).

It's unique in size and structure for the area.How much time and money would it take to get this changed to a legal 4plex, if at all possible?

How long should it be on the market before I decide to try to screen for tenants?

In every case, I direct traffic to our website, which keeps pictures and information about current rentals so that it can help screen some of the traffic.

I have gone thru the password reset process 2-3 time over last 2 days since I couldn't get past login screen ( so clearly I am at least typing in my email address properly lol). 

An investment broker will help find the right property for you with their knowledge of the local market and the ability to run numbers for you on cash flow, and in the property management part of their business they'll be able to take over landlording and fully vet tenants for you through their screening process to make sure the right tenant is in place.

Tenant screening is so important.

Multi-family is good in concept, but carries more risk (repairs, tenants, scalable size etc).