I migrated from Joplin to Obsidian a year or two ago. It was straightforward. With Joplin, I had to use the export functionality from the desktop app. That cleaned up any non-standard bits and allowed for a straightforward import into Obsidian.
Seconding Bookstack. I’ve embedded videos in it and I don’t recall anything special to do it. I also think there’s a way to comment on specific pages…mostly because I remember disabling that functionality.
Agreed on the roles and permissions aspect though. It’s pretty standard to do that for bigger deployments, but it may be a bit overkill for a single user instance.
I run calibre off my desktop. You can enable the Calibre content server and it can serve up your books for download (or provide a web reader).
If you have an Android device, you can use something like Moon Reader (or any other reading app that supports epub or Pdf) to download content from the Calibre content server.
With respect to covers and metadata, Calibre can tag and fill in this info as well - out of the box it will scrape information from Amazon.
+1 for BlueIris. I run Linux almost everywhere else, but BlueIris was easy to set up and has been rock solid (I.e. no intervention) on a Lenovo mini pc (I think it’s @ I5 7500T) and 4 Reolink cameras for years.
Every once in a while I think to replace it, but this is one of those things that I haven’t found a compelling reason to follow through on.