Yah it's beginning to dawn on me that my goal can't be reached via booting off the USB drive due to the fact that it's only used to boot and doesn't contain any of the extra tools like a full DOS 6.22 would have.
fyi before WIN98SE boot, I used DOS6.22 boot from bootdisk.com to construct my USB drive.
I guess my follow-up question would be could I copy/paste those files (i.e. CHOICE.EXE or FDISK.EXE, for sake of example) onto my USB drive and run 'em like I would a command?
Depends where you source the files from.
a DOS installation is really just what you have- you just don't have those files- the external commands, such as choice, installed on the drive. if you do copy them you will need to get the right version. If your using the win98SE DOS you'll need to get the files from Win98SE.