I think I may have been overthinking this. With all the talk about websafe fonts I thought this was hard to do. Looks like typekit and google fonts allow you to do some special online linking and display without the user having to download the font. Will try it out. Cufon sounds similar, but I use typekit anyway.
Typekit's license doesn't allow web fonts to be used in this way. Allowing users to create with or pick fonts would require to different kind of license. One that extends the license to your users.
Right now, Typekit doesn't offer this kind of license for print. Google fonts are open-source and could likely be used for this purpose, though I would read the license for any fonts you choose to make available to your users.
Let me know if you have any further questions.
Thanks - I see that listed now in the licensing FAQ. They do list font-spring as being able to purchase. Would that work? The license looks like $35 ish per font. I'd do that if it worked. Google has a bunch also.