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Good Afternoon!
Yes, that should be possible especially as you're going from an older version of SQL Server into a newer one. You just need to make sure to select the Non-operational recovery completion state (RESTORE WITH NORECOVERY). This is a SQL Server restriction.
More details here:
https://documentation.red-gate.com/sbu/log-shipping
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Also, is there a maximum number of databases the tool can handle?