Until now Imager didn't have any font support on Win32 systems. That's changed.
Both the usual Imager t1lib and freetype1 support now work, using both MSVC++ and cygwin.
With current CVS versions (with -r exp_represent) of Imager you can also use Win32's native GDI font support. So you can use any of those 1000 fonts you have installed :) This works under cygwin too, assuming you have the w32api package installed.