I use Musicbee for my digital collection and I honestly couldn't be happier with the program. Their user interface is excellent. Very user friendly and has seemingly endless customization options. Adding album artwork is super easy, the program can literally find an album cover from the internet on the program itself so copy/saving images from google is never necessary. And I've never once had music just disappear on me.
In terms of organizing my library, I go crazy overboard with playlists. Unlike Itunes, when you add songs to a playlist in Musicbee it groups songs together by album, or at least you have the option to group them that way if you want. I have every song by every artist in my collection labeled by subgenre (black, death, thrash, heavy, etc.) so I've got separate playlists for each subgenre from each country. "Finnish black metal", "Norwegian Black", "Swedish Death", or just playlists by subgenre, "Atmo-black", "War metal", "New OSDM", "Blackened Speed", etc. And within each playlist I have each album grouped together by year, then alphabetically. I also have playlists for my favorite albums from each year going back to 2000, and I always have a separate playlist for new releases from the current year and a general "new music" playlist.
It is definitely tedious subdividing my entire collection into a myriad of different playlists (I probably have over 100 of them) but it ultimately makes navigating my collection and choosing what to listen to SO much easier. I also feel it keeps me from having to make some kind of spreadsheet.