I agree with you to an extent haole. It does come of as easy listening, however I think that might be the nature of his writing as much as it is the choice of musicians. A lot of his recorded music has a very layed back, easy listening sound. Both full band recordings as well as some of his solo pieces. It is exactly that which i had to get used to when listening to his music. Wish On My Star is good example. The band at least offers the oppurtunity for interesting instrumentation is such songs where Jake may not be able to fill out the sound as much. I, at times, get the same "easy listening" vibe from Brittni Piaiva. And less often but still mentionable, Aldrine. They all can border on the Contemporary Acoustic Pop line from time to time, and that is a style I'm not too keen on. But despite it, I still listen to and respect their music and playing.
Also, in both solo and his band excursions, Jake has a tendency to go over the top in the "lead" arena. Sometimes going out of his range of abilities to solo over a piece. A good example is in the Equator video. The song has a jazz fusion vibe to which I don't think his soloing is appropriate. It's as though he has to try too hard to create leads that ultimately end up ineffective to my ears. He is a good lead player in a pop or rock context, perhaps even classical at times. His jazz lead playing, however, leaves a bit to be desired in my opinion. Where as players like Abe Lagrimas, Benny Chong, and Lyle Ritz for example, have the necessary musical vocabulary to compliment the more complex jazz progressions.
None of what I said is meant to detract from my opinion of them as good musicians, and my not be the opinion of others. I understand that fully. They are just mere observations of mine. I have some about all artists I listen to, which again, are not meant to be attacks on the artist.
By the way, what does haole mean?