I got this error under OpenSUSE Linux 11.2 using wine 1.1.28. The problem was the game was trying to read data off of my cdrom drive. Some debugging showed that the files it wanted were really in the "Patrician 1 and 2" parent directory of Patrician 2.
For wine under linux, I had to run winecfg and remove my physical cdrom drive so it was no longer drive D:, remove my linux home directory (Z), and add the .../drive_c/Program\ Files/GOG.com/Patrician\ 1\ and\ 2/Patrician\ 2/ as drive D: in order to get around the "Font not found" problem.
After that, everything worked. Not sure if that helps with Windows installs. My windows Patrician 2 crashes with an obscure 0xc0000005 error on startup, so I never got that far. Possibly it's the same problem though -- the game is trying to read the cdrom drive.