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I've been trying the upgrade scenario today, and so far I have been unable to reproduce this problem.
I created a passphrase-protected private key and used Jenkins 1.480 (with ssh-slaves plugin 0.22) to set up a slave. The slave also uses a different user name than what the master runs.
I then upgraded to Jenkins 1.511, which uses the ssh-slaves plugin 0.23, and I see that the configuration has been successfully migrated, and the slave connected as it should be. So there must be something deeper going on that what it appears.
I do agree with the poor error message. I have just fixed this. This would let us better understand what's going wrong. This error message fix will be in 0.24.