My non-profit the Rebel Tech Alliance is working on a series of blog posts that will look at self hosting for begginners. If you sign up for the blog you’ll get them when they’re published:

blog.rebeltechalliance.org

Or our main website is at www.rebeltechalliance.org

But really what I’ve got going (if you exclude Transmission) is the simplest stuff. Jellyfin, Calibre and Syncthing are just ‘click and install’ - they are all self contained so they don’t need all that Docker stuff. I suggest just tinkering with them.