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since you already have an always-on home server the self hosted route is the easy win, no monthly fee and the library stays yours. the calibre content server works but its pretty bare, most people now run calibre-web instead, it points at your existing calibre library folder and gives a clean web page where each family member logs in, browses, reads in the browser or downloads and sends to their kindle. works fine across windows and android since its just a browser.
cloud (box and the like) mainly makes sense if you dont want to keep a machine on, which isnt your case. the one thing to sort for self hosting is reaching it from outside the house safely, so https and a login rather than exposing it raw.
thats the bit that usually trips people up, so full disclosure i help build an open source project called syncloud that installs calibre-web in one click with the https and per-user logins already handled, running right on that home server you already have. its the low effort way to get the family sharing going without piecing the auth and certs together yourself.
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