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ro: to transfer 20/30Mb files over disk drives are INSANE! Each disk is 720 kb, so in "rough math": 30/0.7 = 42 disks!

openmsx supports tcl scripts in its command console, which can be of use.

You could 'cut' the large files into floppy sized chunks, use wrdsk top put them on floppy disk images, install an autoexec.bat on your HD image that copies all files from floppy disk to hd (COPY B:*.* A: ...) and then run a tcl script that will
- load a disk image
- reset the MSX, so it will run the autoexec.bat
- wait a minute or 2 to give the MSX time to copy the files
- loops over all disk images found.

In the end you'd have to paste all files back together again on the MSX HD...