Deep thoughts, with Zane, since one of my reluctant hobbies is web community management:
Over the years, in the course of discussions related to the stodgy luddite pilot persona, it has been suggested to me more than once that a great percentage of the most knowledgeable among us does not even dabble with these websites. That's kinda sad.
As a 170 owner, I never joined the association because I was put off by George Horn's personality. That's probably more skin off my back than his/theirs, but the point was proven, at least to me, that there are camps among us, divided by technology. Horn was the one who intimated that the majority of their membership does not use the forum (and therefore it was not a priority for him.) I'm sure the same must be true for other type clubs for classics, whose demographics tend toward the older crowd.
We exist in one section of the
Venn diagram of this interest group-- The owners/members who embrace the Internet tools of a type club. There are other members who do not, and there are some of do so with great resistance and make a lot of noise about how difficult it is. After all these years, it makes perfect sense to read Hotrod admit that he only recently got a cell phone.

In spite of that proud ignorance, I think you've done pretty well here Eric. I'm still working to make this particular site more mobile friendly.
Some of us have made a career out of designing products that are intended to make transition into technology by the reluctant a little smoother, but we can only stoop so low. That's not impertinence, that's just a realistic threshold; setting the "suitable for ages 7 and older" label on the box. The tragedy is that there are some guys out there with deep, rich understanding of aircraft construction and history, etc. But the chances of them contributing their knowledge for posterity is slim because of this technology gap, and maybe some stubbornness that rides on the stigma of "computers."
Platform/technology agnosticism like Barnstormer mentioned is hugely important. We've reached an equilibrium of specific open technologies championed by the mobile device manufacturers that has hopefully plateaued for a while. Today the middle ground, the great equalizer, is HTML 5(information), CSS 3 (styling), and MP4 (video), which is how you're reading this on your iPad, your desktop computer, etc and watching videos across multiple devices. The technology should be transparent to the user and not a stumbling block, but by its very nature it is dynamic and in flux and therefore prone to some adoption hiccups. But, no one should ever champion or defend Adobe Flash in the year 2015. This is what happens when airplane enthusiasts are forced to become reluctant information technology professionals.
And finally, when it comes down to a single person who represents a website or club, as is often the case in these websites, that person had better be a damned PR buddhist monk. I have always struggled with this aspect of the job because some days you just can't stand to hear one more person insult or criticize you because of how you choose to moderate or organize your website, so you make a comment or reply in the heat of the moment (sometimes my mouth is faster than my brain.) That user on the other end has judged the entire ball of wax by your emotioned response, and often their only recourse is to "quit" the site. I've been on both sides of that fence and it's just the dynamics of pride and human nature.
Hopefully the Skywagon website guys will learn from this experience and focus on how to remain professional in a volunteer position. I think having these type club websites succeed is critical for owner support.