holes in leaves are not an issue to an otherwise healthy tree ..

your tree is not otherwise healthy ..

you need an onsite inspection from a trained arborist ... mostly because it looks like it will fall on the house.. if it fails.. and thats isnt good ... call the cost piece of mind ... not every guy with a chain saw.. is a tree doctor ...

if you decide on removal.. get 3 estimates from removers. .and insist on them showing you the insurance documents ... its usually cheaper in winter.. and unless the tree dr tells you its an emergency.. you can probably wait until winter ...

if you decide to have the trunk ground out.. have them remove all the grindings and refill with a good topsoil.. or do that part yourself.. after they haul the bad stuff out ...

lets us know what the dr said.. its how we also learn ...

ken

https://duckduckgo.com/?t=ffab&q=isa+arborist+long+island+ny&ia=web

I think you have Gypsy moth caterpillars eating your tree leaves. The eggs usually hatch early May and as they grow so does their appetite. One caterpillar can eat an equivalent of one square foot of leaves a day.

You didn't mention the name of the tree but is it a chinkapin oak or chestnut oak? Oak is their favorite tree. Have it confirmed quickly and take the appropriate action, but they rarely kill a tree.

Disclaimer. I'm not an expert by any means, I just pretend to be one. Any comments or advice I give are based on semi-educated and/or limited experience, and may contain dated knowledge which has been proven wrong and obsolete by advancements in the subject matter. Therefore all advice should be confirmed by an expert.

Thank you all! I contacted local arborist yesterday, should be coming today. Hoping the tree is save able as it's the only tree on the property! Also if they do remove it, and grind the stump, is there a rough estimate how much further around they would have to grind to get rid of roots? The tree is very close to driveway as well as sprinkler lines, which I'm sure would have to be removed and added back.

some suggest .. well i do.. lol .. that the tree is twice as big underground [in mass].. as what you see above ... in the shape of a pancake ..

you are not going to get all the roots ground out ...

trees really dont die when they are cut down.. you need to kill the root mass ... and one way to do that.. is to grind the stump .... but you dont chase the roots all over the yard.... and the neighbors yard.. trying to grind them all ...

you will have quite a mushroom show in the years to come.. as the roots rot ... dont freak out.. its a free show from ma nature ...

in fall.. plant some new trees ... we can guide you through that ... see section one at the link below.. its not really a summer thing to do .... if you want to make it relatively easy ...

as to kevins suggestion ... your local county extension office.. would know if you have a current outbreak of gypsys in the area.. as well as the arborist ...

ken

https://sites.google.com/site/tnarboretum/Home/planting-a-tree-or-shrub