I think the only people that think Essentials, the new character builder, and WotC marketing are failures are people that like to gripe on message boards.
If you don't follow these threads, DnD has no glaring issues and plays just fine as written. If you subscribed to DDI any time after Nov. 16th you have no clue that there was an old character builder.
I think Wizards is focusing on the future and long-term growth. If you're loudly complaining that your specific desires aren't being catered to then WotC probably wishes you would just go away. (Standard boilerplate about this being a generalization and that rational, constructive criticism isn't included, etc.)
From a technology standpoint, new users will be accustomed to using computers and software to accomplish most tasks. In the near future internet connectivity anywhere will be a non-issue. It's already that way where I live and cellular networks keep getting faster. Subscription services aren't a big deal and they will only grow.
Since I got Netflix I can count the number of DVDs I've purchased on one hand. Entertainment is essentially "disposable" and pretty much always has been. Shakespeare wrote plays to make money so he could pay the rent and not to provide high schools with material for drama class many years in the future. Dungeons and Dragons is no different.
For a new player Tieflings and Dragonborn have always existed. Legolas rode his shield just like how it was written in that book the movie is based on. Conan is either a talk show host or the governor of California. Greedo shot first, etc. You are the past and there is a new cultural baseline.
Why should WotC try to offer anything to a segment of the customer base that actively tries to discourage new players, over-scrutinizes everything they do, and proudly boasts about how much product they aren't buying?
I really don't think it's fair to paint people who are voicing what are actually legitimate complaints as backwards grognards that don't "get it" and are standing in the way of progress.
Wizards of the Coast does three things well:
1. Sell books
2. Sell miniatures
3. Sell cards
Everything else they have tried to do in regards to the D&D brand has been an ill-conceived, half-in half-out attempt to expand into other areas. Through incompetence and lack of thorough analysis has caused all of these efforts have either evaporated or fallen short of promises.
Exhibits:
a) Core rulebooks with pictures of vaporware in the back that has never appeared
b) Reduced content in their e-zines
c) Complete revision on the core framework of their software offering, which wasn't even finished to begin with
d) Putting out an "upgrade" of their existing character builder with fewer features than the original product
e) Two month blackout on character builder updates
f) Packaging a choose your own adventure starter set into a box with vastly limited rules that was designed to create nostalgia with its old fanbase. Unfortunately this material was not only vastly incomplete compared to its predecessor, which they forced a comparison to by copying, but certain aspects of it were incompatible with rules publised less than two months later
g) Complete inability to ever publish a single game day adventure without numerous editorial issues that require fixing
Items a through e have to do with not properly understanding the scope or analyzing the issues inherent in an undertaking of this magnitude. This requires senior executive leadership to understand the importance of business analysis and project planning over short sighted and ill-conceived attempts to nickel and dime innovation.
Item f could have been easily remedied with a little market research first. Something like plopping a prototype down at some Cons and asking how it compared to the previous Red Box should have at the very least illustrated it might be a good idea to just give it its own cover art, instead of heralding the return of the Mentzer box.
Item g could be solved by circulating a PDF email throughout the WotC office with a $50 Olive Garden gift card to the person that finds the most editing errors with the game day module.
I like the Essentials books, as a consumer I'll be focusing on those, because they are done very well, until the rest of the company catches up with the publishing. I don't think I'll have to wait long, but I'll definitely have to wait a little while at least it looks like.