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Cool. I think based on what you have said that "Remove selected excess jackets" could instead be "Remove selected legacy jackets". This will give you what you want for when a book has multiple jackets - it will keep the new one.
I think for the sake of any ongoing maintenance in a library it would be better to encourage the legacy jackets without the tags to be removed. That way if at any point you decide to reconvert a book, you aren't immediately creating a problem for yourself of a double jacket.
So I would see the workflow as:
Check having jackets
Select all those epubs and run Remove selected legacy jackets
Then run Check missing jackets
Then do your conversions to add a new jacket.
Under that workflow, you should never have a need to check multiple jackets.
If your library is large with a lot of legacy jackets that you really don't ever intend to reconvert, then you can use Check multiple jackets. However at least this way the Remove selected legacy jackets wil be useful to you without having to do extra check/remove steps after a conversion.
How does that sound?
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