Yes, it certainly would work, and very cheaply if you can find the software;
There was a version of Kermit for the HP that I had once, but I don't have it
any more. I've never seen Procomm for HP Pascal.
The disadvantage of this method is time!
Assuming a connect speed of 9600 baud (max for the HP Kermit I had) then
the shortest possible time to transfer a 100Kb file would be about 11
seconds.
The maximum actual transfer speed is always a lot less than the line speed,
so I would expect a 100Kb file to take around 15 to 20 seconds.
Then multiply that by the number of files to transfer...
Joseph.