@Benjamin BarredoI've been a hands on kind of guy my whole life. so i can wander around a house for a few minutes and get a decent ballpark of what it will cost for a job if i do it all my self, then i double it if i get someone else to do it for me. during my walkthrough i take a bunch of pictures for later reference.then negotiate some terms with the seller and get contract with some contingencies, then do a better analysis.

Like I said, a monkey punching keys on a keyboard and running around with a camera can make a listing look good, and that is why every single STR site has a ranking system based on far more than just pictures and text.

Don't deduct off sec deposit for this.3) Send them a nice DATED letter with before pictures and current pictures of the house exterior.

And from those few pictures, the home looks amazing. 

All the numbers that in there is practically a guesstimate based on the contractors who saw the pictures that I sent him, and I also made the number large  than usual, I could be completely off, but I think I'd rather be off  bigger off too little. 

I will admit that I found it a little weird you were posting pictures of somebody else's houses instead of your own.

The water damage was bad enough to rot the wood underneath, but I don't know how to post pictures on here with my phone :/

It would seem pretty tough to market a contract without having pictures of the property, setting up showings, etc.

We know it needs to be completely rewired electrical wise and the bathroom and kitchen need some work but the house is very livable. 27 Hamilton Street, Haverhill, MA has a few pictures on Zillow. 

I will try to give some respectful inquiry as to what might be done on the sellers part to paint a better picture.