I use a Mac program called BitFont, which can generate fonts for inclusion
in Squeak.  The advantage of BitFont is that it can render any Mac
TrueType fonts at any size.  I've had good luck with making big TrueType
fonts on the Mac and importing them into squeak

http://minnow.cc.gatech.edu/squeak/952

Note that a little while back I reported some bugs introduced in BitFont
importing sometime between 3.0 and 3.2g.  See my email of 22-Apr.
However, these are not major problems.

-Eric