Its hard to imagine how anyone could incur any liability or cause much damage from caulking something and using sand paper.

The home did indeed smell smoky inside on the top floor(though there didn't appear to be any smoke damage), and we couldn't really tell about the roof from looking at it below.

Players of damaged team was so furious that they burned down one Chinese restaurant (they thought that he is Chinese referee) :)And penalty for Brazil is not the only thing that he did wrong. 

Yes you might have a lawsuit later but the damage would be questionable-- See my "crazy idea" below if you choose this adventure.-- Adventure #1Here is another adventure that you can choose--- Adventure #2 DRIVE OVER TO THE PERSON'S HOUSE & TALK WITH THEM DIRECTLY FORGET THE MAILMAN AND PAY THEM MONEY TO BREAK THE CONTRACT.

This was way more damage than my one month's security deposit would cover.  

Then, the third time they checked after the listing agent said it was accepted they see the water damage.

I have placed a tarp over an open roof on a property (to minimize any further damage) and have also done some yard work before closing. 

Some policies cover rent loss if there was damage to the unit and unihabitable for the tenant, as well as landlord legal fees, etc. they may be liable for.

I know it's not a good idea to rent to friends/family but I naively thought it'd be fine.It is NOW, but it was touch and go when he moved out due to some difference of opinion on damages and rental deposit refund.

The gambrel is a unique style that at least provides more adequate clearance, re the upper roof line, than cape cods.The last property I rehabbed had 15 year old wood framed Pella windows that were NEVER installed correctly & this was once a 'model home'.All had suffered severe water damage & rot within the lower frames & sills regardless of any roofing overhang.The studs around the window frames exhibited rot, as well as some of the flooring directly below the windows.