Doug,
I really praise the point of your article. I also love to teach everything I know about the topic to anyone who's interested in the subject, like most amateurs.
Like you said, there's no to little sense of elitism in those groups. But I also know this: Like all the really rewarding things in life, Astronomy requires persistence and solid interest.
I decided to comment your article since I disagree on some things you wrote and that contrast may help people who read it, look at the picture from another angle.
Trying to find Deep Sky Objects or the planets (very easy with little experience and knowledge) in the sky, is where most of the fun is! Having a computer doing it for you is like you own a Porsche and let a chauffeur drive you. The only difference here is that, unlike the chauffeur, the computer has no fun at all!
I didn't find anything interesting on cloudyskies.com, apparently is just a domain for sale. Did you mean www.cloudynights.com?
If your interest is solid, you've got nothing to fear, understanding the sky is a lot easier than most people think.
Diogo.