I never did sucessfully get the OSX method of creating EOT fonts to work. All the software compiled and seemed to work properly, but no matter what font I tried to use, Internet Explorer never used the EOT files that were generated. According to my server logs, IE was downloading the EOT files, but it wouldn't display them. Since then, I've found a new resource for generating the EOT files. FontSquirrel.com has a webform that does the messy work for you. Fonts that did not work using the local method did work with FontSquirrel's tool. I'd like to figure out what they are doing differently so that I can replicate the functionality on my own servers and test environments. I hate relying on a single online source for this kind of thing.
Switching to CSS provided fonts has been a huge success for me. It isn't supported in Firefox before 3.5, Safari needs at least 3.0, and Chrome requires the 4.0 beta. But based on server logs, the vast majority of visitors to sites I've built support the functionality. On one ecommerce site in particular, HOM Lifestyle, I've shaved the page load time by about 50% by swapping FaceLift font replacement with @font-face declarations