Thanks again everyone for providing input & help! I’ve decided to move to a Google Domain and the Cloudflare tunnel setup. I have used the walkthrough by Everything Smart Home as well for the Cloudflare tunnel. Some friendly advice when you start your migration to Cloudflare: Ensure that you have SSH access to your HA host machine, stop the DuckDNS add-on and remove or hash-out any code in your configuration.yaml related to DuckDNS (dont ask me how I know 
).
I have updated the last part of my initial post by adding more troubleshooting methods which have been suggested in this post. This might help others as well in the future. Cheers!