If your computers are running XP SP3 or above, you could use Group Policy Preferences and utilize the files section to push fonts to each computer.
A script would also work and if you do it this way, I recommend using an "IF EXIST" check so that way it only pulls the fonts down once rather than every time.
As for non-standard fonts, it will depend on the program in question how it is handled. Most Office programs will default to Times New Roman if the font you are using is not found. You could also embed the font inside of the file itself, though you might get into licensing issues with the font developer if you do that. For other programs, you'll simply have to check how they react. In short, it might be best to not use custom fonts that are expected to exit the organization.