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Dear pwalker8
I used another library on my Mac (running with calibre 4.15). I was able to establish wireless connection with my iPad Pro 10,5 (PadOS 13.4.1). The App CalibreCompanion started to sync. Again only 40 books were synced.
As you have a subscription: I am not sure CalibreCompanion doesn't know you have a subscription, even if you use another device. Are you using it from within the same local network? is your 2nd device registered by apple (AppleID)?
So actually I would prefer to wait for feedback a) from another USER without subscription or / and from the CalibreCompanion Team directly.
Regarding the money question: How much are you paying for calibre? The real service is the database - isn't it? CC only generates a link between a Reader application and the database. Thats something! for sure but the intellectual work behind this service is much smaller than the intellectual work behind setting up a decent reader application or / and an excellent database.
One last remark: did you try the calibre-web reader? there you can read ePub by using any web-Browser. (still I personally have some remarks on this procedure... but....).
yours
Henning
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