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Your only (relatively) safe method is to run the content server (on the newer machine if possible as it has more features).
You need to really secure your Network and Calibre if your son is not on the SAME LAN. You will be opening a pinhole in the WAN firewall if the server is on a different LAN. (I've seen attempts to get at mine in the routers log. Keeping the port closed except when expected use helps. Oh and I don't use the default port)
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