I'm actually surprised that you could get a USB floppy drive to work, as I thought I remembered reading that the support code/drivers for that kind of storage device has gone missing about two macOS versions back (but maybe I misinterpreted something about that)
Depends on the type of file. Graphics files might zip-up, but not be significantly smaller (because some data types can't be efficiently compressed, among other reasons), so compressed files might not be small enough to fit on a floppy.
1.4 MB of space on a floppy just doesn't go very far, so that begs the question:
Where's your USB flash drive, or why don't you use one? I have seen 128GB capacity on sale under $20 recently (capacity>88,000 floppy disks, on your keyring 😎 )