This is just too convoluted and complicated. What does desktop per-user even mean? Am I allowed to use the font and use it to produce a document if I pay for a 1-5 users license ? or do I have to pay more if that document ends up in the hand of more than 10 users? What if that document end up being a pdf that people might share all over the world? Have I right to use/reference it but not to embed it? What about views? If my blog get 4000 views on a regular basis but a post end up viral and views explode to hundreds of thousands? Am I suddenly in debt with the font creator?
For a start, a webfont is not different from a desktop font. It is a font and that's it.
Just put one single license at 1000usd for the individual one and 4000usd for the pack if you value your font that much for f... sakes.