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You'll need to run it from the command line, unless there's a batch file that passes the --debugwps option to rockboxui.exe.
Extract the font archive to "C:\Program Files\Rockbox Simulator\sandisk-e200-sim-w32\archos\" instead. The "archos" directory is treated as the root of the player by the simulator. The simulator isn't finding the fonts at: "C:\Program Files\Rockbox Simulator\sandisk-e200-sim-w32\archos\.rockbox\fonts\" so it's complaining.
This one seems to be up-to-date with the archos folder...
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