3.) WotC has had a history of partnering up with some bad designers. 3e's E-Tools was salvaged from the smoldering mess its original designer left it in, 4e's the less said the better, and 5e's debacle with Trapdoor shows again WotC has had no luck in picking digital dance partners.
WotC certainly has not had a good track record of choosing successful digital partners. But 4E "less said the better"? We got a very good, very useable 4E digital tool package that you can still subscribe to, if you are still playing the game.
4.) They promise too much. E-Tools/Mastertools promised us online virtual tabletop, including sound effects and animated monster tokens when all people wanted was a char-gen and monster builder. 4e's VTT and character visualizer again emphasized bells and whistles over a functional toolset, and Dungeonscape was spinning its wheels on multi-platform support and e-commerce content sales rather than fixing the damn "not-really-beta-beta" character generator.
All people want is a simple chargen and monster builder, huh? You got some market research to back that assertion up? I certainly don't speak for all "people", but I totally WANTED what WotC was trying to originally deliver with the 3E tools. And they were close to delivering it when it finally fell through, sadly.
5.) Contrary to popular belief, D&D is not an easy thing to code. Sure, it looks simple on paper, but having a character generator that can effectively allow anything (in terms of either future content or worse, user-created content) yet remain stable, auto calculating, and functional is a tall order. 2e's Core Rule's 2.0 + Expansion is perhaps the best D&D software ever made, and even with the expansion allowing custom classes, lots of workarounds, limitations, and "note this on your sheet" stuff.
Totally agree here!
6.) We forget this is not limited to D&D; Magic the Gathering has a long, horrid history of electronic issues as well.
It does? I certainly remember some less than stellar Magic games, but both the current Magic Online and the Duels of the Planeswalker series of games seem to be doing very well.
I would hazard to say that ANY licensed property has a mixed record of good digital offerings.
7.) In short, WotC has been been lettting perfect be the enemy of the good. Even when things have gone good, they've had more setbacks and roadblocks than any company should rightly deserve.