I agree with your assessment of Jupiters Travels and think it is on a higher level, so to say, than a book like Odyssey to Ushuaia.
BUT... I really enjoyed Odyssey to Ushuaia. Maybe it helps that I am a 23yo male and can relate to his current (at the time he traveled) position in life, but it was an easy read that was entertaining and displayed a lot of the day to day stuff that goes on as well as a little bit of culture and some technical traveling topics such as border crossings. I love the deepness of Ted Simon, but also appreciate the more light hearted style of Odyssey.
Long Way Round annoyed me at points because of the seemingly constant whining, but I never really got that feeling from Odyssey.

I liked the Motorcycle Diaries OK, but I actually think I prefer the movie. The book did become boring to me at several points.

I've also read " Mi Moto Fidel". I think the person who recommended it to me hyped it up too much. It was good and entertaining, but didn't stand above anything else that I have read. It did give me a lot of interesting information about Cuba, though, and is probably what made me go out and by The Motorcycle Diaries.

I'll just throw it out there that, while not a book, Erin and Chris Ratay's travelogue ( www.ultimatejourney.com ) is what I stumbled upon that originally gave me the moto travel bug 3-4 years ago.