I am running out of space on my 5TB drive. Can I use a USB hub and add another drive? Or should I just try something different like attaching a larger drive?
Yes you can attach a hub and second drive
Is there any additional configuration required?
Also, does it need to be a powered USB hub--or can the pi handle it?
Powered
Always powered external USB drives with a Pi, and do NOT hot swap them! The Pi will likely reboot if you try that, which is a known issue.
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