We listen to jazz all day long (www.kcsm.org, usually) and I'm pretty knowledgeable. It is a fact that some of it it highly technical playing that can be difficult to actually "enjoy". Yesterday was a piano piece that was some odd modal thing heavy on the technique. It was interesting but maybe not exactly "pleasure". I would steer newbies to what some call pop jazz or the like. Not, probably, "smooth jazz", which is Muzak. Spyrogyra, Jean Luc Ponty, Lee Ritenour come to mind. Jimmy Smith was very accessible, and there are many others. Another thing that I miss myself sometimes is singing. One of the things about jazz is that so much of it is instrumental. Singing gives another dimension and can humanize it a lot. Of course there are many great singers. Diana Krall is easy to get. Stacey Kent has this precocious voice and also bridges that gap, largely.