You must be aware of this fact to insure that the property remains a good investment. 

Look up local ordinances, laws, taxes, and insurance.

We rent out our previous home and bring in $600 a month on it after mortgage, taxes, and insurance, but she doesn't see it as an investment property and so it has been hard to continue investing without her support.

Established the LLC, EIN, business checking, business insurance, accounting, etc (all the boring stuff) 2.

If your insurance coverage isn't enough, they could seize the LLC assets, but not your personal assets.Additional thoughts:1.

If this was a standard rental process then yes, I'd recommend going through the process of applications/screening steps, a background check, and then require the deposit; since it sounds like the house is being rented to transient workers though, the very nature of the work situation calls for a bit more flexibility on the renting end. 

I just listened to yet another mastermind class in sure you've heard of it,  WREIN, and as much as if love to join that I'm already in one... but knowing if this is a great option.   

He’s been in the industry for 20 years, I believe he started in concrete work, the last 5 with his own handyman LLC and 4 months ago got his GC license, bonded and insured.

- or should I have the owner of the unit below me file a claim with their insurance?

For context, I am a doctor with a stable income and was able to put 20% down comfortably to avoid insurance.