I've been very lucky so far with no damage. 

Security Deposit is for damages (typically) and can only be uses after the lease is over and tenant is out of the rental.  

The old growth trees which appear to be impinging on the house could be viewed as a negative in terms of potential damage to the house in a wind storm and to the foundation / basement over time.How does this house's square footage stack up against the comp.'

I do know the buyer lost and it wasn't for the price of the house but for damages, financially in thousands of dollars as well as for the emotional side, changing schools along with the hassle factor.

I did not list him on the 3 day pay or quit, as he is no longer residing there.Second, is it generally allowed to add other damages to the proceedings? 

She just left the property on Sunday and I did the walk through to assess any damages and immediately was hit by a very strong smell of cigarette smoke.

It has some foundation damage and the electrical panel is outdated.

I am more looking at it as that most of the others have been torn down or destroyed (hurricanes, structural damage, etc.) and these are the ones that happen to be left.  

On one there is a large hole in the roof that's been there for years meaning there is probably significant water damage and mold inside.  

I ended up with some damages, but I was able to resolve with the person renting.