You can have 10 layers of LLC but if you drive drunk while driving your LLC owned truck hauling supplies to your LLC owned rental and you wreck and injure another you are liable period.

Wouldnt he be covered under my homeowners policy though if he does get injured?

MA is a "may issue" state, so they can refuse to allow you to defend yourself (gotta love socialism), but you can feel good knowing that they'll put the guy in jail after he injures or kills you.

A dog that size can seriously injure a neighbor or anyone else. 

And I'd wonder why you wouldn't want to reduce your liability by doing so.Second, what happens if you don't pull some permit and it results in a tenant getting injured or killed?

Based on what project managers typically do, most full-time project managers would be classified as an employee, and that means you'd be responsible if they got injured (that's what worker's comp is for).

This cuts down on my exposure risk because if someone should get injured on your property, you know what's coming next.

What if i am injured?

Hi Jason Gerasia and Rob Parmar,Thank you both for this conversation.Jason: I have been considering the idea of having a tenant manage the snow removal but am concerned about liability with regards to the tenant getting injured. 

The main reasons for the insurance are total loss from fire and the liability coverage in case a tenant was injured or killed on the property.