I’m anal about my music. So, in iTunes I use Smart Playlists. First issue I need to replicate in Roon is to create a random list of X songs that have not been played since a certain date, say 1/1/2020. I then need to save that as a fixed playlist.
I then want to be able to play the songs from that list, by Genre, randomly, until I’ve listened to the whole list.
Then I start over the process.
Hi @Enoch_Carver, and welcome here !
I’m not sure if what you want to achieve, is possible. Before going into more detail, perhaps it is useful to clarify something to the community 
. What does this mean ( italics part):
I understand what playing randomly means. And I understand what playing by genre means. But (perhaps it’s just me) I cannot grasp what it means to combine those two. Would it be possible for you to explain this, or give a simple example ?
So, I want a list of, say 100 songs chosen randomly out of the library with a last played date prior to 1/1/2020.
I now want to only listen to the classical tracks on that list.
Welcome to the forum.
Unfortunately, I can’t see a way to do exactly what you ask. However, one way to do something similar would be to go to the Tracks Browser, select Focus and then look for Played in the Last 3 Months (for example). This would show all tracks that you have played in the last 3 months.
From there, click the + on the selection to change it to -. Now you have tracks that haven’t been played in the last 3 months.
Save this as a Bookmark and name it something like: Tracks Not Played in the Last 3 Months.
When you want to listen, select the Bookmark. Now click Focus and select a Genre. From there just click Shuffle and listen for as long as you like.
Note, the next time you open the Bookmark, the tracks you listened to won’t be there (but will return in 3 months).
Hope that helps.
Cheers, Greg