((tl;dr version: I'm unhappy with Gleemax and think Wizards has made almost every possible major mistake in their design of Gleemax))
One of the things I disliked about Gleemax was the sudden shift in personality. I suppose it could have been chalked up to the edition change, I think that the style and feel of Gleemax didn't suit the community as a whole. The basic ideas behind Gleemax, which I think could have been described as being "add more of a social network feel to the entire hobby games experience that integrates online play, forums, and blogs" is something I don't think is bad at all, given that for some people, online is the only option, while the others which go online tend to be the enthusiastic fans which are their best word-of-mouth advertisers, and are therefore the two groups most likely to respond well to a well-designed social network. But here's the thing: Wizards seems to have no clue about how to design for the Web, or frankly for computer gaming in general.
But there's an example of a group who "gets" how to design for the web, and how to design a social network in general. Their wide success shows that a social network can actually last, and that it can make tons of money for its creators. It's also a social network that came out of the idea of getting people together that might not live together anymore, though it has since expanded beyond that initial goal. It's called Facebook.
So, believe it or not, Facebook is actually a pretty good comparison to Gleemax, on the basic face of things. And it's pretty illustrative, because it shows clearly how to appeal to a mass audience, and how... not to.
I'll try to run down what I think are basic guidelines that illustrate the difference between a successful and a not-so-successful social network.
1) Know what you want to be first, and focus on becoming that before trying to expand.
Online college yearbook (with extra features) is a theme that described Facebook's initial stages well. It also happens to be simple, concise, and one remarkably resistant to feature bloat in the early stages.
As far as Gleemax goes, "Be all, end all portal for an entire mini-industry" was and still is a bad idea, because it has way too large a scope, at least for the present moment. Official community site for Wizards? Decent idea.
2) Maintain direction, but don't alienate the people you're ostensibly trying to get on your service in the process.
While there has been a few flaps at Facebook,but by and large, they've produced a ToS that everyone can live with and a site that does what it promised to do, so it's easy to keep people from making it a muddy mess, because they know what they want from it and they get just that.
On the other hand, the Gleemax ToS is driving away some devs, and many of the core WotC fans hate the general design of the site, so they are alienating the people they need most, and the reorganizations and apparent actions are causing a section of the fandom to believe they're not wanted.
3) Don't emphasize any one group and try to find a design everyone can live with, even if it's somewhat standard.
Facebook's visual design isn't all that amazing, but given that the groups have such disparate tastes and interests, it does remarkably well at providing a default nearly everyone can live with. It is also something that won't look too out of place if seen at the office, an important consideration for many.
On the other hand, Gleemax displays a marked habit of WotC to favor it's CCG unit, deserved or not. The name comes out of an in-joke that almost no one outside of the company would get unless they keep up with Magic intensively. It is also a design that completely dismisses those of us who don't like to go to MySpace style websites that tend towards the visual assault side of things, or who can't because they are at work.
4) Keep the skeleton of the design simple and don't release until it's done.
Facebook has kept the basic features simple; photosharing, group features, a basic communications thing to keep up with people. They kept it in dev until those features worked well and weren't all that buggy.
Too many different development angles going on leads to missed ship dates and muddled, buggy designs. Example: the Gleemax alpha. It's basically the forums + a really bad blogging engine right now, buggy as all get out, and any further development will make the problems there even worse. Plus, the alpha's inflicted on everyone, rather than a small few (like say the dev team + a few chosen outsiders under NDA) like it should have been. There is still attempts at adding more features, but I suspect they'll just make the whole buggier and buggier. I'd like to see stability addressed before more extraneous features are added.
5) Don't screw with a working formula unless you have a replacement lined up that is obviously better in comparison.
Facebook's kept the core the same, and added features to make the entire whole work better. It has never totally changed things up, even though it has occasionally made minor changes to expand the total possible audience.
Wizards decided to cancel a contract with the producer of a set of relatively popular set of mags while Wizards was waiting on a new product to come out, and before they had provided a clear path to an "upgrade" for many while also canceling them in such a way as to do maximum PR damage to themselves. They also changed the formula behind the replacement to those mags, so much of the fanbase decided that the new formula wasn't for them. They then released the buggy new product that was the ostensible replacement while everyone was still outraged. And then proceeded to not fix that.
Needless to say, I'm totally disenchanted with Gleemax as Wizards has presented it. This is perhaps not entirely separate from any considerations of D&D edition, but it is a significant barrier even if I reverse my position on 4e from where I am now (my skepticism is probably not going to change much) particularly as Wizards has clearly shown themselves basically incapable of presenting a proper online offering in the past and is bungling themselves up in the present.