For those who are tracking this thread, I need to clarify something.
When using the "MS_PRINT_MGR" type printer, ALL versions (WF5, Creo 1, and Creo 2) incorrectly rotate TrueType fonts (on portrait oriented drawings). When using the "POSTSCRIPT" type printer with the "PRINT /D" command, WF5 and Creo 1 incorrectly rotate the TrueType fonts, but Creo 2 keeps them oriented correctly. There was apparently some software change to how portrait orientated drawing are sent to "POSTSCRIPT" type printers between Creo 1 and Creo 2. This same change needs to be made for "MS_PRINT_MGR" type printers as well (and preferably pushed back to WF5).
Unless PTC comes up with a better solution, it looks like I will either have to create PDFs directly and then print those or fall back to using "Stroke Fonts" (with the disadvantages that come with it).
Tom U.