If you really see potential and like the overall quality of the property you may need to get creative on making sure you're covered if the units take longer to lease there. 

Are their listings detailed with good-quality photos?

At least with this method, you could also skip nasty HOA fees from condos.

Louis are higher than the national average, which can impact tenant quality and property values, so thorough neighborhood research is essential.

Doing this analysis in this point of time is a lot like using the "Enemy Method" that Avery Carl from the Short Term Shop talks about it.

In my acquaintance's experience, one of whom has triple digit number of loans being serviced by them they have produced quality and reliable results.FCI is another large, well known servicer used by many people in the industry.

BRRRR is a timeless strategy, I might also recommend "house hacking" and "Subto" as some beginner-friendly methods to build your real estate portfolio. 

I am curious, has your friend mentioned anything about the quality of life or benefits from an investment standpoint outside of affordability?

You should check on the state's laws where your property is located, and (as always) check with an attorney.If you use this method, the two main questions to answer are, who will be the (initial) trustee and who be the (initial) beneficiary.  

I'm willing to pay for the information, templates, etc, but agree there's a lot out there and hard to determine the quality of any of them.