In reply to "Points" are meaningless.:
@Robert --
* I cannot use typefaces with weird licensing requirements. I don't want the user of my site to have to specify how many copies of the calendar will be printed, whether their use is commercial or non-commercial, etc.
Such comments tell me there are a lot of things besides the point system you don't understand. Personally I think you are setting yourself up for an expensive FAIL because of all the things you don't know.
Forget lawyers; hire an experienced production artist, even as a consultant -- someone with about five years or more of experience. If nothing else you will learn a lot from them.