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Unless you plan to remove the actual HDDs from the existing USB external enclosures and install into an eSATA compatible enclosure, you can't connect 8 USB drives to 2 eSATA ports. At best, you could connect 2 of them.
You could connect all 8 USB drives to a powered USB hub. Performance would not be great, but you could access all of the drives as needed. Something like this:
Unless you plan to remove the actual HDDs from the existing USB external enclosures and install into an eSATA compatible enclosure, you can't connect 8 USB drives to 2 eSATA ports. At best, you could connect 2 of them.
You could connect all 8 USB drives to a powered USB hub. Performance would not be great, but you could access all of the drives as needed. Something like this: