I've had many issues with my macbook too, and I think I just found out the problem! I don't know if it's the same for you, but I am having the "License checkout timed out. What do you want to do?" message everytime I open the software. I've had this problem on december 2023, and somehow it went away. Now, suddenly, it came back and there was nothing I could do about it. It has been a week now that I try to solve it with the Autodesk support team. I tried EVERYTHING, nothing would solve it. After trying the clean uninstall to reinstall everything again, the software wouldn't even install, nothing would happen. By chance I went to a different place with another wifi connection and tried to install it and it WORKED! Everything working normally. After coming back home the same issue came back. I tested again with different network connection and it became clear that that was the problem. As soon as I changed connection the license would work or not. So I just found the problem and now I'll try to fix it. Maybe you are having the same case, try with a different network first. I'll see what I can do now and come back here with the veredict.