Took Manolo's proposed approach to font loading on OSX and it works pretty well.
If anyone else is interested in loading application private fonts at runtime, I've added it to my dummy font-loading demo (should be attached if I remember!) to illustrate programmatic loading of fonts at runtime for OSX, WIN32 and X11/XFT platforms.
The "demo" also contains a (smallish) dummy test font, based on (and very much cut down from) George Durous "Musica" font, which has a pretty generous license, so it is not beyond the bounds of possibility that we could clean this up as a working sample to add to the "examples" folder.
(Or even build the loading of private fonts into fltk as a helper function - "fl_load_private_font()" etc. - is that the sort of thing people would use? I would, but then...)
Have fun.
Builds for me with "fltk-config --compile load-app-font.cxx && ./load-app-font" on all tested hosts.
(The WIN32 test was done in an Msys shell with mingw, but the code should be VS compatible too!)