I don't really have a fix but library structure is one of the key things with PlayIt Live.
There are two approaches I can think of really.
1) Structure your library to match rotation rules. You could have artist and album track groups conceivably but unless you want to play every track in an album that probably isn't sensible.
I have selected tracks in decade groups but I don't have very demanding "clocks" to fill.
2) Forget about the library and assemble a folder of tracks for a specific programme by copying files from the master library.
Then ingest that folder as "Programme - Date" into PlayIt Live (thus doing the track analysis) and then drag the tracks from that group into the schedule in the order you want to play them.
Once you have your folders of tracks, I then suggest adjusting the level (using MP3 gain or similar) and you can make you programme/stream.
My "master" library is structured by artist then album (I can also recommend KID3 https://sourceforge.net/projects/kid3/ ) for fixing metadata issues and getting/adding artwork.
Fundamentally PlayIt Live isn't iTunes but it aims at a very different use case.
All of my music library is sorted by album title, but I can't see an option anywhere to show the "Album" fiend in the playit live software.
Having the ability to turn on and sort or filter by the Album tag would be really helpful. Anyone got a workaround or am I missing the obvious?