You can select Yes - the "unknown state" basically just means you won't know what files are and aren't copied.
As far as being "nagged", you can turn upgrade notices off in our Preferences.
If SD! seems 'stuck' it's likely copying a large file. Drop me a support message and I'll help you determine what it might be.
As far as trying to run a "simple backups script that didn't work", I don't have enough information to assist.
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--Dave Nanian
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