While B&O is not adding any new features to the BeoSound 5, they are doing a great job of still supporting it. The "BeoConnect" mac app is just a simple app that transfers the music files over to the BeoMaster 5 hard drive. BeoConnect still works great, but even if it has didn't there are other ways to get the music over to your BeoMaster 5.
The BeoSound 5 does everything that I need it to do. I personally don't like having to use my iPhone -- therefore, I don't find the Essence to be attractive. However, if you do want to use your iPhone, you can connect an Airport Express to the Aux input and BAM -- you have Airplay. Another great use of the Aux input is to connect a BeoGram turntable. I Have a BeoGram 9500 connected to mine. The BeoSound 5 and the BeoGram 9500 each sit atop a BeoSystem 1 cabinet. It seems as if they were all designed to go together perfectly.
I love the Spotify integration. You can even save favorite albums, artists, playlists, etc,. from Spotify and trigger them with macros from the Beo6 and/or MLGW/BLGW.
With the prices of the true BeoSound 5 as reasonable as they are now, I can't imagine anyone trying to save a few bucks to buy the watered-down Encore.You definitely don't have the 2-way Beo6 communication with the Encore. The Beo6 control is just VERY COOL! You can search your library from the Beo6 and you get continuous cover-art on the Beo6 to show what is playing.