The other problem is that Moodle can be a nightmare to upgrade, especially on older installations. At least in the olden days, the DB migrations were not super

The other problem is that Moodle can be a nightmare to upgrade, especially on older installations. At least in the olden days, the DB migrations were not super solid, so you'd run into issues later due to that. But worse, it seems like every school has a few pet plugins that are absolute garbage but they have to have - and either aren't maintained, or have horribly broken upgrades.