I love seeing this as it is one of my biggest frustrations in the investment game. 

Biggest challenge is actually maintenance, finding workers you can trust.

Injuries are the biggest lawsuits, but even those are primarily settled out of court and paid by insurance.

I'm trying to plan this out as well as possible to avoid any issues down the road.I've seen the stories where people run into issues meeting this requirement and get scrutiny from the IRS, to me it seems the two biggest red flags might be when they hire a property manager and also when they rarely go out to the property to work on it themselves, always relying on contractors.

My internet provider said that for $10.00/month additional, they can provide live streaming TV services (i.e.

Sounds like your biggest worry is buying something that becomes a hassle. 

The biggest take away was my ability to utilize machine learning for this process.

To all aspiring house hackers and those aiming for a single-family primary to hold it as a long-term rental, what are your biggest frustrations likely keeping you from jumping in the game? 

Many so-called "income properties" don't produce nearly the kinds of returns we see advertised on the internet. 

I think the biggest issue, is the fact that there are so many social media influencers, with huge followings providing misinformation which leads many new investors to have a false sense of "education".