If all goes well, I'm building the courage to surrender to the challenge. 

I’d love to hear from others who have navigated similar challenges or have insights on improving profitability in the short-term rental space.

What’s your biggest challenge so far in analyzing those deals?

See the chart from Fair Isaac Company (FICO) below: FICO Score Pct of Population Default Probability 800 or more 13.00% 1.00% 750-799 27.00% 1.00% 700-749 18.00% 4.40% 650-699 15.00% 8.90% 600-649 12.00% 15.80% 550-599 8.00% 22.50% 500-549 5.00% 28.40% Less than 499 2.00% 41.00% Source: Fair Isaac CompanyAccording to this chart, investors should use corresponding vacancy+tenant-nonperformance factors of approximately 5% for Class A rentals, 10% for Class B and 20% for Class C.To address Class C payment challenges, many industry "experts" are now selling programs to newbie investors about how Section 8 tenants are the cure.

You're facing a common investor challenge: learning from experience (and sometimes mistakes).

@Blake McWilliams This is a most challenging problem with both residential and commercial investors.

However there are tenants out there who look to exploit technicalities in leases and that is one of the reasons  why lease language is so important.  

Getting one property and cashflowing it will be a challenge. you can try seller financing but you are still going to be highly levered which just enhances the risk that you are taking on.The best way to grow is to focus on managing your rental, saving money through your W2 and crushing that - if you are a realtor you will make more crushing it as being a realtor than over leveraging real estate - then save for down payment and buy slowly. its not a rush.

An eviction will make it challenging for her ever to find a quality rental in low vacancy areas.  

Challenges?