is it possible to use wine in a telnet session to start a (command line) windows application?
Yes.
I get the error that x11drv can't connect to a display (which is correct). I'm also not very sure that the windows program itself does not perform some graphic related queries (there were some fixme messages when I tried to use 'ttydrv').
If the application directly or indirectly loads GDI32.DLL or USER32.DLL it also load the x11drv with the result above if DISPLAY isn't set.
Any ideas? Is there any workaround to use a dummy display or whatever?
In addition to the ttydrv (as you meantion above) you can use VNC like:
vncserver :1 export DISPLAY=:1