Third, what is the potential cash flow? 

To explain what I see is a lot of potential investors and investors with limited exposure go down a rabbit hole and spend countless dollars they do not have because someone is trying to sell asset protection to them.  

I wont disagree but you may find that PMI is worth it to get into a specific deal potentially. 

There is quite a bit to learn so I would say get moving - read, go to meetings, consider working with someone who can help you jump the learning curve, set meetings with potential team members.

I just want to know if this dream is feasible and if I can potentially get some advice from you all. 

Not married yet + HELOC + you not contributing to the purchase all make it rife with potential bad endings.3.

The cops contact you and ask did you ever see anything suspicious, you say yes and the next thing you know you're being prosecuted and also potentially sued by the kids' family for punitive damages.  

The chance of me picking a color that every potential buyer would like is slim at best. 

You can file complaints at DSPS file a complaint https://dsps.wi.gov/Pages/SelfService/FileAComplaint.aspxIf it were me, I'd look up the PM company and then also do another search by the owner's actual name in WI CCAP https://wcca.wicourts.gov/case.html and if there are other similar cases....you also may be able to find potential attorneys that represented defendants and would already be familiar with the plaintiff. 

I will continue to learn about the property classes and how to apply it to potential investment purchases!