The second blog is an really interesting article and I wonder if Gleemax in it original conception was meant to foster that user generated content?
I may be wrong but it was my impression that Gleemax was supposed to be a social networking site for Gamers of all stripes with the added benefit of being a Safe Harbor for producing (for free) content based on WotC IP (i.e. Greyhawk, Forgotten Realms, Mystra, Al Quadim, etc.) and your own private material.
WotC would get rights to that content if you posted it on their website.
Gleemax over promised and waaaaaaaaaay under delivered. Basically there were sites out there that were doing Web 2.0 that could be adapted quicker and more feature rich than Gleemax could without handing over your rights to WotC.
Now, we have things like iplay4e.com and Obsidianportal.com doing things that Gleemax only dreamed.
I think that DDI is a small step in the right direction but it is handicapped by you are in or you are out subscription system. I think they would make more money and get wider adoption by releasing a free, working core kernal of the game and then offering specials, additions, and upgrades using micro payments.
Basically a the first hit is free model.
Having re-read Square Mans'
The Inevitable Future of Tabletop Gaming again I am more convinced that unless WotC and D&D start opening up their IP to broaden its acceptance instead of ratcheting down with things like the GSL they are providing an opportunity for another company or start-up to claim the Micro payment/Augmented Reality model and leave pen and paper D&D in the dust with young tech-savvy gamers.
BTW, Ryan Dancy poked his head in the comments section of Square Mans blog. He is pretty bullish on the idea of a smart phone driven gaming space.