I guess it's a matter of where Love is most valuable to this team. Whether it's being on it or turned into assets. Looking at that extension, yikes, there's no way this guy should stay here for the duration. He has very little chance of playing up to those numbers when he's 33/34.
The longer that Love stays here, the more risk of him falling of a cliff physically and then becoming a net negative because of his contract. Although it might slow the development of the young guys to trade Love; Love's floor spacing, passing, and IQ can be replaced to an extent.
Love loves Cleveland and has given this city everything. It's time to let him finish his career on a contender and let them be strapped with his contract when he suddenly turns into Ryan Anderson. Because you can only wait so long before you're stuck in a situation like Houston is with Chris Paul.
I really, really don't want to see Love moved now, but at the same time I don't want an upcoming roster to miss an opportunity to become a contender because they got sentimental about keeping Love. It's all about 2020 and beyond, not 2019.