I have properties outside Loop 610 and they have been great to me.You mentioned that you are uncomfortable with networking, then I have to challenge again. 

VRBO and Airbnb platforms make it pretty easy to self manage.Find a great cleaning company that can handle turnovers and be your eyes and ears and a handyman for small repairs and you are pretty much there.You can use sites like TAKL.com to find other services that you don't routinely need.

Now i'm not saying buy just any deals, but you'll do your best learning when you are uncomfortable.

This person in particular is not local to me so I feel uncomfortable trusting they have "done millions in transactions", and I don't know what type of materials to ask them for to prove legitimacy.

If you have a business or sales background, lots of things with having will seem routine. 

Sounds like from what you described there are a lot of things that make you uncomfortable about this property and sometimes it’s not just about the numbers.

“people feel uncomfortable buying a property they can’t see in an area they don’t live in, and fear has a lot to do with it.

Tenants should learn the definition of habitable and inhabitable before they go down that road, but if you've taken the time to read this far, you know precisely what I am talking about.Now, I must tell you that sometime in the middle of these texts, I told the one girl in a group text with the other, as they were both bombarding me with pictures of some lint on the floor, a cobweb here or there, etc... that I FELT VERY UNCOMFORTABLE WHEN WE SIGNED THE LEASE ON 2/29 AND THAT SHE SHOULD KEEP HER FREAKING HANDS OFF ME IN THE FUTURE.   

I feeling extremely uncomfortable with the situation, as is my escrow.

After doing this for a while and creating a routine you should have a pretty solid idea of what you want your adult life to look like then start looking for jobs that will start you down that path.If that path requires school then great do that, but don't assume that you're going to just going to be able to do this without schooling because you can't just walk into a laboratory and call yourself a chemist.