The dos program will likely only print on LPT1 anyway. (The usual parallel
port)
USB dos printing is generally not supported by the printer drivers. If the
dos program does not see LPT1,
the parallel port may not be setup correctly in BIOS and windows. Win98 will
support a generic text printer,
with the generic driver, or various printers that print ASCII text in a
compatibility mode. (Usually Epson ESC2, or MX emulation)

To show the flexibility-- I have an older Canon 620 bubble jet. It will
emulate an epson dot matrix printer, (including color versions).
It has ascii text capability, with multiple built-in fonts. As a windows
printer, it functions quite well in graphics modes.
The simplified drivers work well over a peer to peer lan. One of my routers
can act as a TCP/IP print server. This works (most of the time) with the
620. (The printer does occasionally have paper feed problems, and due to the
simplified drivers, the user will not be notified.)
Many of the newer printers no longer support ASCII mode directly, and
require a printer specific driver to work at all. Many of these printers do
not provide classic dos printing support. They may or may not support dos
programs running in a window, or allow the dos program to print to a file,
which is later printed from windows or a windows application.

Using the 620 above as an example-- The printer was new in the early win95,
late win3.1x days. Third party printer support software (used mainly for
photo printing and color correction, as well as multiple page on page
printing) worked well thru early win98 versions. From that point, the
windows printer support modules changed enough to cause problems. By
win98SE, the third party software was basically unusable, and upgrades were
no longer available.

This sort of explains why some of the older printers and driver versions
don't work very well, or at all with later windows versions.