I have a list of about 20 properties from him, I just don't know how to start to the assessing process.  

You should start creating a pitch deck with a financial analysis / summary and market study to share with people to get them excited about the project. 

I started my real estate adventure by purchasing 2 single family houses in Oklahoma with 2 cousins, mistake #1.

It's a little ways away from Charleston, which has kept it off the radar, but it's starting to become a more significant beach destination.

However, given the price points in NYC, I am looking to southern CT so that I can start small for my first project.

I am planning on not resigning my lease and starting of my RE venture. 

The decisions and actions you make today can lead to incredible long-term benefits, so it's great that you're starting now.A good starting point is connecting with a lender that aligns with your goals.

take @Nicholas L. advice and start to go to meetups. 

I started 2 deals with these guys within a couple weeks.They have been a nightmare to work with.

I personally HATE maintenance, so i find jazzy ways to "trade" that with tenant.