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For me, it's option 2. It would be all about pulling down the books that I had added to calibre that weren't already transferred.
I think I'll eventually end up with maybe 10,000 books, so the 30 minute+ timings are a concern. I think what I'd like is to be able to do a download of the complete calibre metadata on command, separately from "normal" CC startup. I could fire that up when I went to bed or otherwise had a chunk of time I wasn't going to be using CC and wouldn't care how long it took. Maybe a second CC start icon on Android that did the complete transfer, leaving the "normal" icon to do what it does now.
"Preparing your books" for my 2200+ books is now a momentary operation and I'd love to keep it that way, while transferring books is actually quicker wirelessly with CC than it is using USB connect and lettered disk drive on my Nook Simple Touch. If pull would significantly increase CC response time, I'd rather do without and continue to push.
The way I do things, I keep all my books on all devices, using calibre to "check-in" new arrivals and clean up the metadata so they sort correctly, have complete and accurate series information etc. Unless I get a new device or a major boo-boo wipes out my CC, I won't be pushing or pulling thousands, or even hundreds of books.
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