Jim, actually I agree with your overall point that the tenant is risky; I just object to the way you took her multiple jobs and single mother status and extrapolated a whole life history out of that without knowing the facts or the person. 

A great book is FLORIDA FORECLOSURE SALES: HOW TO BECOME AND STAY WEALTHY BY MASTERING OBJECTIONS, MARKETABILITY, AND POSSESSION Paperback – December 29, 2021by Natalia Ouellette Grice Esq (Author)Although it is Florida based it is a great place to start learning. 

You can always go into wholesaling, flipping, or whatever the next shiney object is, but House Hacking will always build wealth. 

A real estate investor’s strategy should be dependent on the individuals financial means, available time to commit & and objectives.

And than we go to "mission" to fight the battle to achieve our mission objective. 

I am actually in the middle of discovering that process myself, and it has been a roller coaster of emotion, but I have started feeling experiences of how trust in other people can get you achieving the objectives faster than we think.I have got several off-market deals in Central Texas currently available, and can help you learn a thing or two about our market down here, and more than happy to refer you to folks in Illinois.

So my goal is replace my w2 income and objective 1 is cashflow (not the negative kind!).

Listening to too many other investors will give you shining object syndrome... also many of local investors, and millionaires I talk to locally have said they creating most of their networth owning San Diego real estate.   

Tap into that, as there is a lot to learn about the business, but don't chase shiny objects and get too bogged down. 

The additional objections you mentioned, I'm willing to address as they arise, and preventing through contract addendums.