Hi Megan -
Welcome to permies! We're over here across the ditch and in my region all the big old macrocarpas are coming down everywhere you turn. The main things driving it here are
dairy farmers not wanting them, because if cows eat the foliage they can abort, and just the general mindset that old trees need to come down :-( As a result, some of the sawmills that used to work this timber are shutting down and it's getting hard to find sawn macrocarpa (but there still seems to be plenty for sale as firewood...what a waste). I try to use it instead of treated timber wherever possible. Needless to say, the value of good-sized standing trees is going up all the time, and that is probably the case where you are as well. I don't know what level of commercial planting has been underway, but there is lots of Leyland cypress grown in the central plateau.
100 years is probably middle age for these trees in our climate. 200-250 looks to be the lifespan in their
native habitat, but given the way they grow in NZ I wouldn't be surprised if they can get much older in a good location. If you're not grazing cows and look after them, they shouldn't have or cause any problems. Maybe you could talk him into just harvesting one every five years for milling, provided he plants more for your grandkids. They're pretty amazing trees.