Switching property managers seems like it was a smart move, especially with how much you and your wife had to step in before.Chicago definitely isn’t an easy market, but it sounds like you’re set up for better success moving forward.

It's just a question if they are willing to share them.Sure I could build these out, but I am much better at buying houses than I am setting up CRMs and am hoping someone out there would be up to helping another investor out. 

Set an AM time that makes sense and PM times that make sense.

Your cabin will be set apart by the above, not by things you can get at Lowe's or Walmart. 

Of course, some of the potential tenants want flexible terms at start to get themselves set up in the space. 

Does anyone have a set of questions or things they think through or scripts or anything that helps them approach, talk to, and close on deals with homeowners when they approach them directly (whether through mass marketing, driving for dollars, or otherwise)?

QBO isn’t made for REI out of the box, however, it is an amazing tool and really has amazing reporting when set up correctly.  

What a great set of answers and advice!!

We do currently have around $50k set aside for our next downpayment as well (that’s in addition to a $25k emergency fund).

We are primarily looking for land on which to set up an owner-occupied situation with 1-4 rentals.