Work your butt off and stay as far away from student loan debt as you can.

I highly urge you to protect yourself first, otherwise there will be no one you can help.

You can do a few deals make some cash then get your license..This makes the most sense and I recommend this strategy to my students.

I'm to the point now (didn't pay taxes with that amount like I likely should have) where I have the urge to do this again.I'm looking for deals now like I was before march, and realized there are things I need clarity on, and by clarity I mean full details no vague answers.

My medical resident recently up and left saying his student loan payments just ballooned and he could no longer afford the rent. 

Consider student housing see below.Locate and attend 3 different local REIA club meetings great place to meet people gather resources and info.

However do consider that if you are going to continue to rent to various college students these kinds of situation could and do arise so you might put some wording in your lease that will help your renters manage the use of the building and resolve or prevent common disputes. 

The second factor was this will allow me to completely pay off my student loans and be able to direct that money into more investments.

Your work in education serves and uplifts the minds of your students.  

Here's a good post on selective enrollment education at Whitney Young.https://www.dnainfo.com/chicago/20160202/morgan-pa...10,000 students apply annually to be admitted to the Near West Side high school.