I think "guarantee" would even be realistic since it would be impossible to grant. Have done a software contract or two in my day, you have to review the various scenarios.
a) Shawn may at some point start charing for DNN. The only viable way to do this would be to say something like version 5 and forward will be $$$. At that point you still have 4.x and below if free is important. Now since a lot of the potential income would be paired with 3rd party modules, closing it wouldn't really be an option, so worst case you pay a license fee to deploy DNN. Less worst case members of core team split off and maintain the 4.xx version.
b) Shawn get's hit by truck and his evil girlfriend now owns PMI, she flies worldwide and seduces the entire core team (even Nina) with her wiles. Worst case you pay a huge license fee to deploy new DNN. Less worse case you maintain the 4.xx version version yourself.
c) Shawn get's tired of all of us making fun of his hairdo and stomps off in discust never to view DNN code again. Worst case, core team finds a new benevolent dictator and after a period of drifting in the wind, continues on. Best case, books with Shawn's picture become collectors items, we all make millions off eBay.
Often companies will have a "source escrow" clause that means if the company ceases operations they have the option of taking the code and maintaining it themselves. This isn't needed in the DNN case since you have it and can maintain it in perpetuity as long as you don't try to create sidelines and market them as DNN.
So in terms of risk, I don't think there's much of an issue. Let's also face the fact that in 5 years there'll be something totally different to learn and deploy. Even if you bet the farm on DNN, you certainly have to have a plan B around because even DNN will change because even a "guarentee" isn't worth the electrons it's magnatized.