I have been renting it for 6 years now and am wondering if it would make sense to do one with that townhouse as well or not. 

Selling an existing, well-performing asset has some risks.  

Their pictures of the leadership team is sketchy as well. 

I am hoping to learn more about how investors analyze their deals and make decisions, as well as looking to better understand general real estate investing.

He has helped a ton of BP members successfully house hack and has done it himself as well and can provide you with invaluable experience.

Based on the info in your post, my recommendation would be to turn these assets into well oiled machines and max out their NOI.

Well there is somethings right here and some are off mark IMHO.

For instance, cities like Chicago are known for landlord-tenant laws that skew heavily in favor of tenants, and that risk should be baked into your underwriting.What’s your take on balancing short-term cash flow with long-term equity growth?

Alot of unknowns as you don't have the ability to walk the property beforehand, but interesting process, and pretty good deals exist there.While the Trustee Sales are cash purchases, there are many hard money options that can turn over the funds in time for the 24 hour funding required to complete the purchase.If you are interested, let me know and I can go into more detail, as well as make some other suggestions for you to consider. 

And it can work really well for you as long as you pay attention to the statute requirements.In order to defer all tax you are selling investment real estate and buying investment real estate of at least the same value you sold.