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| Does the target server need to have RedGate Backup Pro installed? |
Yes it does.
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| When should I take the backup that goes on the second server to be the basis for the log shipping? |
Usually off production hours so as not to affect your users' activities, but that would depend on how long the backup would take and if your production server has more than adequate CPU and disk I/O to spare for the backup.
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| How do I insure that the shipping starts up smoothly if the database is in use? |
You can take full and transaction log backups even when the database is in use.