Hmm... The first error does sound like an update that hasn't upgraded the database. That happens, because WordPress auto plugin upgrade doesn't trigger plugin activation for some reason, and you have to manually deactivate and reactivate the plugin for that to happen.
Unknown column 'content' sounds a bit worrying, particularly as there's no index on that column.
I wouldn't worry about the duplicate key error.
Anyway, if you want to play it safe, you can always remove old versions and do a clean install of the latest version.
