@Matt Charette For a second investment I see many challenges and a few red flags.

I always rooted against him growing up.When I dug into his story I realized he has a lot in common with Michael Jordan.

No red flags.

Long-story short, I decided to stop using it as an Airbnb in the fall, stopped taking new reservations, and planned to wait out the guy that was planning on staying through January to either put the house up for sale or get standard long-term tenants in.The guy stopped using Airbnb because "his bank wouldn't allow him to pay through the platform" (red flag, I know) and I allowed him to pay me separately through PayPal every month.

HML telling you to pay $3,000 up front for access to their software and services is a major red flag for me.

Absolutely any advice, red flag alerts, creative tips, other perspectives will be received and appreciated! 

Kyle,Probably the best way to vet them is by speaking with other real estate investors and listening to their experiences.Two other red flags would be...1.

I vetted their history as standard and no red flags came about aside from them being private contractors.

If they do not have references they may be new so tread lightly, and if they refuse to provide any references, this could mean they burn bridges on each deal and is a red flag.

Listing agent says tenants have 800 credit score, but I think this is a red flag!