You may want to consider dockerizing your services just for maintainability and isolation from your host. I recommend something like Nginx Proxy Manager to serve as the “main entrance” for your docker network and to handle Let’s Encrypt for you.

Yes and no. It’s great for hiding your IP and preventing DDOS attacks, but it does require you to use their certs, which means they technically have access to your data. Cloudflare is pretty trustworthy, but the risk is still there.