Have you tried clicking 'no' when you first connect the quest, and then click enable link from the quest dash ?
Yes I have already tried that
I was having the exact same issue, and like many people, i was having to reboot my PC/restart the Oculus app to get Link to work. I've since discovered how to get Link workig perfectly every time. In spite of the recommendation, do not open the Oculus desktop app first, leave it closed. Enable Link on your headset, and allow the Oculus app to execute by itself. Link will work every time! Hope this helps someone 🙂