I have started my research on management companies in the area and will take your suggestions and learn more on this topic!

The best part is the free CD is nothing more than a bunch of vague suggestions about how you can make all this money in real estate and vague bragging sessions about how he has been around so long and wants to give you all his knowledge before he croaks (paraphrased) Someday I will be completely immune to the crooks attempts at separating me from my hard earned money.

Just curious on possible strategies or suggestions from anybody currently thats an agent in the Central Illinois or Chicago area.

That’s okay—what’s important is understanding the "why" behind your investment decisions.While your accountant’s suggestion is a great starting point, make sure investing aligns with your own goals and situation—not just because someone else is enthusiastic about a particular strategy.

I walked all the nearby comps, gave the seller my opion/list of what his property was "missing" (fenced yard, light staging, add a 3 board fence panel and landscaping here...) and advised him to get a surveyor to mark the lot corners...The previous agent had not suggested they get a surveyor to mark the lot corners when he bought the property to flip....there's a chance the house or driveway may encroach the neighboring property.  

Narrowing down the options will probably come down to comps and city/neighborhood specifics; things like permits.Any good suggestions for finding out how long permits are taking in certain areas?

@Kareem Hammad With that amount of a down payment, I'd concur with @Julia Lyrberg suggestion about house hacking and expand from there. 

Isaiah, I would suggest starting out with doing some research on some of the available platforms like AirDNA.

I suggest you find other sources of income or partner on deals to grow your real estate portfolio.  

Quote from @Stuart Udis: @Danielle B What data are you relying on that suggests Section 8 leased properties provide for better returns than other investment strategies?