Sorry if this question is trivial. I have always just been running my Squeezecenter/SBS as a standalone server on linux. Would this mean i would have to switch back and forth between my local server environment and the online "mysqueezebox.com" music source?
I will give it a try.
Nope. SBS will do everything MySB does. SBS uses MySB in the background for Apps and Music Services.
Using SBS you will never know MySB is being utilized. It is transparent to SBS, your server UI, and your players connected to SBS.