My opinion is to NEVER hire tenants to manage something like this

There are only a few things that I'd need to hire out.

I plan on hiring a property manager, if creating my own LLC is recommended to prevent any legal issues. 

If its resi in a certain area or comm RE in multi-units, call them and explain what you want.They'll appreciate an aggressive attitude and will almost always hire juniors. 

Suggest he hire an employee if he needs day to day help.

With that said cash flow doesn't equal taxable income.Why would you be scared or something when you can hire a professional to take care of it for you?

I'm new to the world of land lording but have hired dozens of people in my career.

You are going to have to hire someone who knows what they are doing and hope you not just throwing money out window. 

Hire things out if you have no time for managing. use the money you make now to live personal expenses and use cashflow from properties to save, scale and acquire more assets. 

We've reached out with: attempt to create a partial payment plan, provided info on every relevant grant or assistance program available to them, provided info on local employers who were hiring, and offered cash for keys if they moved out.