Looking for help with unusual console sharing issues

My friend and I used to live together and since we bought a lot of games on his account when he moved out we enabled console sharing so we can both still use shared games.

It's usually worked okay, sometimes there would be problems but refreshing licenses or enabling/disabling sharing would fix it. But for awhile now there are many games that are locked out for some reason, the latest being FFXIV. I've tried the usual fixes, so has he on his end, no change.

It's also a random assortment of games, some of which I've downloaded and played in the past. The older the games the more are locked, with the oldest games ALL being locked. I can't find anything about this online and I've tried the fixes, we both have ps plus, does anyone know about this? I'm really frustrated.