@Ivan Johannes , Thanks for the question. From the description, I see that have spent good time on troubleshooting this issue and I understand it can be frustrating.
If you haven’t tried these already, kindly try and let us know how it goes:
Please do a DNS lookup on your domains with https://www.digwebinterface.com – check if the A record is pointing to the correct IP address on the App Service.
By default, your app uses a shared public IP address. When you bind a certificate with IP SSL, App Service creates a new, dedicated IP address for your app. If you mapped an A record to your app, update your domain registry with this new, dedicated IP address.
I’m not sure about the certificate you’re using. If it’s a Private certificate, ensure that it meets all the requirement.
The free App Service Managed Certificate and the ASC already satisfy the requirements.