The Font Squirrel app is very handy, it can make functioning .eot files out of some of the fonts that the open source ttf2eot converter folds on.
No reason to not embed fonts liberally now. Using a CSS type reset toolkit will help normalize web-friendly fonts, they may tweak some of the attributes of fonts in general so little things like the spacing around embedded fonts are consistent. If there was complete consistency, you could ditch creating graphics out of some things in your template such as your navigation bar where custom fonts are utilized.