Music
Can I transfer my music from my desktop computer to a flash drive and then transfer it to my new iPad?
iPad 2, iOS 9
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No.
You will need to use iTunes to sync music from your computer to your iPad.
There is no standard flash drive that will work with a nearly 9-year old iPad with a unsupported, over 3-year old iOS version.
You might be able to use special wireless, WiFi hotspot built-in style flash drives/hard drives that move and stream data from drive to iPad and iPad to drive over WiFi using the drive maker's special iOS Apps.
These types of drives are made by Western Digital, Seagate and SanDisk ( also a Western Digital company ) and may still work with your old iPad.
I make no guarantees.
Good Luck to You!