Music players, text editors and file managers are 3 sensitive areas where I usually choose a "nearly right" candidate, only to come back searching for something better after some months of suffering the small glitches and misses of the "nearly right (but not perfect)" choice.
PSPad is my text editor of choice... but every now and then I try to find something better. xplorer^2 is my file manager, but the same happens. Then it comes music. It used to be Winamp in the early days. Then came MediaMonkey, which I still find pretty good. Then came JRiver which is quite powerful, but then it was back to MediaMonkey. Then I found MusicBee... It's been 3 I think. I haven't looked back!
Many MANY features, but still it doesn't feel bloated, slow or hard to navigate. Things usually work just like I expect them to. I must confess I tried to manually implement something similar to the INBOX with MediaMonkey. Imagine my surprise when I found the feature completely implemented in such an elegant way in MB! Transcoding is really customizable but simple at the same time. Reorganization works like a charm. Look & feel, inspirated on iTunes (in a good sense, I mostly hate iTunes) is clean and elegant. Though every now and then I still need to resort to mp3tag, I do most of my tagging on MB. Device management works quite well. The hability to use Winamp's DSPs is a welcome extra. And the way Steven stays close to the community and releases so often: awesome! Updates and features and more updates and more new features, but the original "spirit" remains.
Powerful but simple, great performance, good for the newbie and the power user alike. And free!
(I will donate, I promise).