The data on that USB drive will deteriorate over a couple decades. NAND memory generally isn't an adequate format for archival purposes.

Indeed. The BBC’s Domesday book was put on a pre-CD glass based optical medium which should last forever, but they managed to lose reading equipment for it, and a huge digitization effort from the 80s would have been lost (they published a call for help, and eventually someone found a reader in their garage.... but it was a close call)

Yeah I see online empirical data that shows anywhere from years to centuries, depending on temperature. So not thousands of years.

A future civilization would need to reconstruct a compatible operating system, software and hardware first, then build something with a USB port to put the stick into.

It's not impossible but consider how many ancient human languages we still can't translate, or can only translate due to coincidence (as in the case of the Rosetta Stone with Egyptian hieroglyphics.) Translating digital information in a similar cultural vacuum would be exponentially more difficult. If that stick is encrypted, how does one even know there is information to begin with?