I'm giving a lady friend one of my 'old' Raspberry Pi 2Bs, it had whichever version of Debian Wheezy was current when the 2B first came out, but as my first Pi, it was frequently if ignorantly apt-get upgraded.
My problem is about offloading some important files to a flashdrive. The PNY 8G seems to be properly mounted, and I've transferred individual .pdfs, .mp3s, .pngs, .txts, etc without a hitch. The trouble is a folder that contains several saved webpages that are two parts: a file & a folder containing the numerous page content files. (They are the Adafruit setup instructions for their old #1983 2.8" Touchscreen hat.)
When I try to copy the archived parent folder to the flashdrive, I get a message that it already exists on the drive- and what do I want to do? The only option Wheezy gives is to overwrite the existing files, but the newly created parent folder sure appears empty. So do trying it with any subfolders.
What am I doing wrong?

Also, I'm wondering if an upgrade to Jessie on a 2B runs smooth; she only wants a surf, mail, and smart typewriter machine and has been using Ubuntu on a very vintage Acer for a while without panicking. That still means basically a GUI user...