We have a significant housing crisis here, and it adds insult to injury with so many empty properties that were bought as investments. 

You certainly want him to have this just in case somebody gets injured on the job, you do not want to be held liable to pay this guy salary for a long period of time if the injury is serious.

Yes - major issues (death or major injury) will mostly likely involve a lawyer on contingency.  

The downside comes in two different forms:  If the investment doesn't work out and you incur a loss, you'll add insult to injury by being left behind with debt to pay off. 

Yes, the landlord will have to pay the legal fees deductible on its own liability insurance, and will also suffer incredibly intrusive inquiries into every aspect of its business and personal life as the parties engage in "discovery" during the lawsuit.A third party who trips over a tenant's child's bicycle on the front sidewalk, and suffers injury and medical expenses, will look for somebody to sue.

To add insult to injury, ex "sold" the properties for about 25% of what we paid for them over 30 years ago! 

I had a traumatic brain injury and after all is said and done I have about 60K to invest (and 30K in bank) but I don’t have a W2 or 1099 to show the bank.

What happens if someone slips and falls on the property, suffers a horrible injury, sues for $1 million, and wins?

Under HUD regulations, any house or apartment that has four or more steps must have a handrail installed to prevent the potential for injury.

The biggest fear probably lies within the fact that investing is an irreversible process.