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I don't believe it's a font issue. Here are screen shots selecting the same font Courier on the same file on the two different Windows systems:
Windows 7
http://img691.imageshack.us/img691/3953/textpadfontwin7.png

Windows XP
http://img832.imageshack.us/img832/7158/textpadfontxp.png

Selecting ...

Ben,
Sorry I mis-typed. Yes, the character in question is not 254, but ASCII 20. The "lower-case thorns" display correctly, it's the other ones that do not.

I wasn't even aware you could change the font in TextPad. Can you point me in the right direction to the menu item?

Also, any thoughts of why ...

I too have a similar issue. Textpad is not displaying certain ASCII characters correctly in Windows 7 environment. Specifically ASCII 254 (little black box). This character is a specific delimiter for a filetype we use all the time (Concordance load file), and Textpad acting weird about it, is ...