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Answer to first question: Yes, this kind of upgrade is available in Fedora for 1 month after release of the new version so it should work for you and I successfully upgraded from 25 to 27. (I had minor problems with selinux and missing status icons but I don't know if this was related to skipping 26.)

To the second question: I'm not sure. I have no experience with encrypted harddrives but I recovered broken systems a few times so there might be a way but it will most likely take some time and patience.