Keldryn
Adventurer
Because, in my opinion, it was awful. I'd get annoyed about every 30 seconds while trying to use it. Good riddance to Silverlight and the slow, bloated platform it created.
Silverlight itself was actually a very good technology. The terrible performance of the character generator can be attributed to the fact that every action you took triggered a call to the web services on WotC's servers. Every time you selected an option, the program had wait for a response from the server. Had the data and the rules to apply them been stored locally, the app would likely have been quite responsive.
But yes, the inability to run on the dominant mobile platforms was the nail in the coffin.
My point is this: this app is very functional and looks good. It was (apparently) made by one person in his free time. So it strikes me as very odd that a team of 2-5 professional programmers working on this for 20ish hours or more a week wouldn't be able to make a similar but much more expansive product.
It's not a question as to whether or not they are capable of doing this. It comes down to the weighing the costs of developing, testing, maintaining, and supporting the application against expected revenue. A desktop application designed for one user to access locally-stored data is an entirely different and more complex beast than an application in which many users access a shared remote data store. You can't just write an application, call it done, issue an occasional patch, and have one guy answering support calls/emails between 9 and 5 PST on weekdays. You need a full-time team dedicated to maintaining and supporting it (even if it is a small team). Customers will expect it to be available 24/7, which means that you need that 24-hour monitoring and support.
Once you allow the datafiles to be stored locally, it is only a matter of time before any encryption is broken and the files get distributed on torrenting sites. Unless those making the decisions at WotC are prepared to accept this, then they have to go with the more complex online application.
It's an apples to oranges comparison. On the surface, it appears to be a difference in degree, but I would argue that it is a difference in kind.