Ah, I see what you mean with Museo – although I am not familiar with its licensing. This is sort of the trick with the idea of simplicity – it doesn’t facilitate choice very well because it can’t handle options. Most people like both options and simplicity, but they don’t always sit well together.

I’m assuming that users of a service like Typekit will read and understand one-time, blanket terms of use like “for web only” and that such terms would apply to all available fonts in that service. There will always be a place for information about rights and warranties, but it might be made simpler if it were to apply to many typefaces at once.

A single license for large type families would make things much easier. The example I was thinking of when I suggested that faces within a family might have different terms is Jos Buivenga’s Museo Sans – only certain faces are licensed for @font-face embedding.

Services like Typekit won’t solve the issue of having to read a license – there will still be a license you must agree to and you will want to know what you’re signing up for there, too. Aside from that, I imagine that the license would cover use only on the web which would mean that if you wanted to use the same font for a print campaign, you may have to purchase a separate license. I’m not sure it’s dead simple if you have uses beyond the web.

By the way, a large type family would be covered by a single license, so there wouldn’t be the need to examine numerous licenses per font, just a single license for the entire family and all its small caps, ornaments, etc.