The whole problem with Gleemax is that WotC didn't understand what it takes to create a decent web application. I'm a web developer and their main issue was that they had forums created with PHP (a modified vBulletin, I believe) and decided to do the Gleemax site in ASP.NET, with the ASP.NET site acting as a gateway between the two for single sign-on. As any .NET developer knows, ASP.NET doesn't really like to work with PHP, and vice versa; what they should have done was chosen a single platform and created a new application from scratch that had both features, but they wanted to rush to market and keep the current forums going, which is an understandable idea, but one that just doesn't work in software, ever. It's never a good idea to have two "critical" applications written in two different languages and expect them to work together. - the sheer amount of work involved makes it almost always better to pick one platform and rewrite the legacy stuff to use it.
Also, the fact that most of the technical aspects seemed to be created using the standard Microsoft "drag and drop" approach (I have no proof of this but the way the app worked seemed very much like the standard ASP.NET controls with code behind stuff, not a proper n-tier architecture; just smile and nod if that makes no sense to you; I'm a programmer

) meant that the code was neither scalable nor extendable, so they would have run into a boatload of problems down the road for not properly architecting the web application. Coupled with the fact that the forums were, and still are, buggy as hell (I remember when they were down regularly dozens of times per day and WotC's only response was "MySQL can't handle the number of posts we have" - proving they have no competent technical staff whatsoever since MySQL can scale) made Gleemax doomed from the start.
The concept was great, and if I ever get around to it I might revisit my own D&D Social Site idea that I tossed around right when Gleemax was announced (I called it "18 Charisma").