@Scott M. is correct.  2 different things.The LLC shields your personal name from most lawsuits.The Insurance policy (General Liability + Umbrella) provides the funds to settle the claim.

To protect yourself from Liability claims from the tenants, you agent needs to endorse the Homeowners policy with Landlord Liability.

He told me never to file a claim on an old roof just to get a new one, and the claim will follow me and hurt me for years?

These would simply be to determine your taxable gain.You will however have depreciation recapture taxes due, for the period it was a rental, whether you claimed it or not. 

Rather than doing a clean quit claim deed, we went with a more convoluted setup with a NNN Lease to our combined LLC.Originally posted by @John Underwood :That is great!

Tell the tenant to go after the previous owner for their deposit in small claims court. 

You for sure have a claim.

You can claim a $1500 tax credit per lead certificate when you get it in MA which helps offset some of the cost.

However, I am wondering if there are other types of insurance I need to get to cover myself and my partner against tenant claims of injury or sickness.

I just saw a youtube video claiming that if you don"t set it up in the state of the property then you wont be able to do evict a tenant in that state with an out of town LLC. does anyone know if that is true?