Hello @katesfb, I do not know using WiPy1 with pymakr over USB. I tried it shortly with WiFi, but I had to modify pymakr to get it working. Pymakr as a product is about to be abandoned, so do not expect any further support. It seems that most people just give it a try and then use other methods.
Resolving the USB error depends on the operating system you use. Since you mention screen, it seems to be OS X or Linux. The error indicates that you either specified the wrong port or pymakr is not allowed to use it.
WiPy will also not appear as flash drive. For file exchange, you have to use ftp or other tools which use the USB/REPL connection like ampy, rshell, mpfshell.