It’s not risky to have a tall tree removed. They saw off the smaller branches first, then bring in a crane and park it on the street and someone goes up in a bucket; they put a chain or a harness on the tree parts and bring the big chunks down that way. If there’s room, they just let the big sections fall to the yard (they only bring it down in a harness if there is a fence or something it wall fall on).

My neighbors had tall trees that were too far gone from emerald ash borer and they were sick of paying to treat annually. Now they’re just waiting for the roots to die enough to put in some new (not ash) treees.

A competent tree service will take it out without any damage. But if the tree is healthy and just standing there minding its business I would leave it be. Unless you have several thousand dollars burning a hole in your pocket.

I would absolutely keep it. Mature trees are things money can’t buy, and add a ton to the appeal of a house for me. If it starts to die, obviously you take it down right away. But a massive healthy tree coming down for no reason whatsoever is heartbreaking. I would never buy a house in an area without mature trees.

We have an ash tree that is still healthy but needs to be treated yearly to prevent death from the ash borer, and of course pruned every couple of years. It is extremely tall (about 3x height of our house) in a very dense neighborhood with small lots. According to two arborists, it's still healthy, but it's reasonable to remove it as well (nobody would want to remove it if it dies as it becomes brittle). Honestly, I personally always worry when wind storms approach...Our neighbors like the tree and would hate to see it go. One reason I would consider keeping it is wondering if it is a big asset when we sell. It is the only substantial tree on our property (though a couple of others on neighboring lots). Thoughts?
Another worry I have is how risky it is to have such a tall tree removed in terms of damage to property/fences/retaining walls...?