If I remember correctly, the screen full of '$' appeared when I set the Webplayer in "diagnostic" mode under the original OS. After a very long wait, that Virgin logon screen finally appeared.
Can you tell us more about your BIOS settings? Here are some quick notes on the BIOS settings which you may or may not have:
-To get into the bios, unplug your webplayer and plug it back in.
-While your webplayer boots up, press F2 (the second key to the right of esc) until you
get into the bios.
-You will be asked for a password, it is schwasck
-Under the "Main" tab, set the primary master to "auto".
-Then, under the "Advanced" tab, Change "installed O/S" to win95,
and "Large disk access" to DOS.
-Then go to "I/O device Configuration" and change "Local bus IDE adapter" to primary.
Can you type in CLS to clear the screen and get the C: dos prompt?
Hopefully with some more info, we can help you.