I would encourage you to continue with dedicating your downtime to learning as much as you can, building up some capital with a job while you learn, and obtain some kind of business plan to get started.

I would encourage you to keep house hacking as an on going strategy as its an easy way to acquire multiple properties over the course of a few years. 

I always encourage everyone looking at Chicago to focus on buying in the best area you can afford though.

First off I want to say I that I am sorry for your loss.As far as where to start off it really depends on what your goals are.Do you want to just do fix and flips, rentals, air bnb, combinations.I highly recommend you do a ton of self education from books and podcast, get a mentor if you can, and ask lots of questions.I always encourage people to never be a one trick pony.

I would encourage them to sign another lease.....either MTM goes up....$40/$50/$100 month or stays the same if they sign another lease....of course it depends on market rent.   

I would encourage you to look for properties that have an unfinished basement.

@Kenneth Donaghy Thank you for the suggestion; It's encouraging to see that people younger than I am are doing well with the right mentorship and partners.

This updated guide came out this year and is better than before, but it still encourages fraudulent claims and we will continue to see more and more service animal requests.

This is an encouraging win!

That so encouraging and true.