One of the best opportunities for training with great paddlers has now become common at major paddle races. The biggest surfski and outrigger races typically draw many of the world's best paddlers some of whom typically provide either multiday training or daily training runs that can be signed up for well in advance. Downwinders in surfski or OC doubles with a champion can be an eye opener. Races such as the Gorge Downwind Championships, Canadian Ocean Racing Champs, and Maui to Molokai will have several training opportunities that will be advertised (and often fill up) well ahead of their associated races.
There are now some companies that are combining training around races with full support packages for your paddling before and during some well known races.