Firstly, as with @DNSB, I have loaded a lot more books at a time than the low hundreds. I have needed to sign out recently on my Clara HD and it loaded the 8000+ books with no issues. If I was loading in bulk, I'd probably do it in batches of 2000, but, that would mainly be because of the timing.
For your steps:
Why have you separated sending the covers? If you are always uploading the covers, then enable the option in the driver. That will do it each time you send a book and you don't need to remember to do it.
Again, for step 8, just configure the driver to do it automatically.
And to me, a step is missing to work out why the failures happened in the import. That way I know I won't have issue later.
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