Gleemax was a steaming pile, but they really did a good job turning around after that. Their new DDI toolset is actually quite good.

I must admit that I've been very surprised at how well they've executed over the past year. Like you say, in the past they've been pretty poor.

MTGO3 will be replaced by a web-based version that looks a lot more promising. I think WotC are aware of their weaknesses, and taking steps to correct them.