Does grandfather receive medical benefits that he cannot have real estate anymore/ which prevent him from needed Medicare?

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?

I am wondering if anyone actually did that before.Any tax issue by doing that, such as How to claim the interest expense, as the mortgage is under my personal name, but the property is in LLC.