The place shows well (I might take down a few photos and the cat tree but otherwise looks good). 2.

The downfall is parking off the street and la huge tree standing by the side!

The drain cleaner guy pulled out a nested clump of tree roots.

My husband was over at that property trimming the limbs off one of the trees. 

Can I buy the property and get the same tax benefits even though the trees are now old?

I said "no" but added a fee for tree based 1800s style payments.

I bought 700 acre tree farm in Oregon in 1999 for 1.7 million...

LOL - I think it's more likely that someone was jumping on the roof (there is no attic in this area), or a limb fell on it when the neighbor was trimming the trees. 

But how should I deal with this tree situation?

.… 1-Haul in dirt around foundation install window wells 2- cut back trees that are too close to the house 3-clean gutters forget gutter guards most if not all do not work for various reasons 4-increase the  size of gutters, make sure gutters discharge  10' , I buy black drain pipe burying it discharge far away from the house.5-Sump pumps is the last thing to do. they are noisy.