I managed to find a workaround to my own question.
In the Radarr Discord, I stumbled on a message stating that almost nobody is using the internal SSL code in each app. In fact, there was disagreement whether it was even being maintained and tested, regularly. They said everyone is using a Reverse Proxy.
About the same time, I happened to find this page Synology: How to Allow Plex to Work Over an HTTPS Connection? – Marius Hosting A very detailed walkthru on setting up a Reverse Proxy to go into a Docker Compartment. Exactly what I was looking for. Just tested in with all the apps, and it appears to work great. He has other walkthrus for the Plex ecosystem. I haven't looked, yet, to see what else he has.
Hopefully this will save someone else a lot of searching.