First, we should find out what's out there and who, if anyone, has already taken steps in this direction.
European Americans United has put together a
School of Western Culture page showing a substantive collection of classics. In addition, these classics have been transcribed onto the site and are available in HTML format (hat tip to Kievsky for wising me up to this resource in the first place).
http://www.europeanamericansunited.org/school1/