Transferring data from FreeDOS to the cloud is something I need, but not able to achieve over WiFi, mind you, my FreeDOS computer is a netbook.
So, I believe the easiest way would be to install a Linux distribution alongside FreeDOS. The 30GB HDD offers enough space for doing so.
With a Linux on the machine, it will be easy to boot into Linux when data-transfer is needed. Reading and writing from a DOS partition is something that Linux is able to do since a very long time.
I went for Linux MINT Tara i386, just because I had a USB thumb-drive with that particular distribution readily in my drawer.
Concerning the installation, nothing special to report. I decided to use 14GB for Linux and left 16GB for FreeDOS, plenty for both operation systems.
After installation, FreeDOS did not boot from GRUB. It turns out that one needs to boot FreeDOS from a thumb-drive and re-write the system files using the "sys" command.
What FreeDOS is concerned, that's it.
The native screen resolution of netbooks can be a low for your GUI on Linux.
However, resolution scaling works beautifully, should you need more real-estate on the screen.
Here are two tiny scripts I use to toggle scaling:
$ cat nb_scale1
#!/bin/bash
xrandr --output LVDS1 --scale 1x1 --panning 1024x600
$ cat nb_scale1_5
#!/bin/bash
xrandr --output LVDS1 --scale 1.5x1.5 --panning 1536x900
Enjoy toying with DOS and Linux on a small netbook.