Live oak are great, but like mature magnolias, they create a ton of work. Once they get over 100 yrs, they nut twice a year (sound familiar Augie??). They drop leaves twice a year (right now, coincidentially its like a leaf blizzard outside), plus grubs love the roots and moles love the grubs.
But its pretty amazing that mine have been standing for at least 150yrs, made it through hurricanes with almost no damage (Hugo, Floyd, Matthew since Ive been here), and stand about 70ft tall. In those same storms Ive lost all type of water oak, pear, gum, etc.