I don't think he's lurking on the message boards, but he's definitely aware of the front page. He emailed me a while back when I mentioned him in one of my articles, before he was working for WotC. I had jokingly called him out about copying my idea for a Coldsnap article referencing 1984 and he just wanted to say that he didn't realize I had written something similar and wasn't stealing it. I clarified that it was only a joke, since I didn't really expect anyone to be reading my stuff, but he said he would keep an eye on this site in the future. I also sent him an email later on, congratulating him when he got his current gig.
My guess is that Brian Strand wanted to get some of his writing published and since he's friends with Digges, he asked his advice. The article he submitted really isn't the sort of thing that they'll accept at StarCityGames (unless you're already established and/or have won something big) and you have to be on the writing staff to submit anything to MTGSalvation. So Kelly recommended this site. And I think it's a pretty good fit, since a lot of our stuff is just story telling.