Those trees look like they were pruned in the past by Morticia Adams!
Gruesome.
They would compliment a Gothic "haunted house" look, but yours looks too nice (and too normal) for trees like that, or gargoyles.
I agree that a sugar maple poised to puncture your roof is not worth the risk even if it could be radically pruned into some kind of reasonably healthy shape.
If the other one really is a cherry, maybe it is valuable enough to be very severely pruned. Then see if it grows back into less of an eyesore over a few years.
If you don't mind waiting a few years or more for new trees to grow up, I'm sure that would improve your yard's appearance and property value. In the meanwhile, they serve as poster children for "this is why trees benefit from CAREFUL pruning".
I enjoyed the photos!
By the way, when you had the property inspected, did the inspector mention that the sugar maple was a roof-killer waiting to happen? If he didn't, and had no disclaimer that excused him from looking at the elephant in the room, he deserves to be scolded or at least educated.
