When solutions create more problems

This will be a brief post, but it's been awhile since I've posted and I wanted to put something up, even if it was mostly an "aside."

THE PROBLEM
I listen to a lot of music and have several thousands of songs in my iTunes library. The problem with having so much music is that it can be hard to organize it and listen to songs I know I like while maintaining variety. If I only pick the songs I know I love, I end up just listening to a smaller and smaller subsection of the total library as it grows, leaving tons of songs sitting idly, unlistened. Yes, this is pretty mundane, but it is a problem I wanted to solve.

THE SOLUTION
One of the great aspects of iTunes is its "Smart Playlist" ability, where you can automatically generate playlists based on a number of factors. To re-introduce songs I hadn't heard in awhile, I created a playlist called "Listen Again." At first, I just set one parameter:

-Songs that I have listened to at least 10 times (showing that I liked them at some point) but haven't listened to in more than 2 months (showing I have forgotten about them).

This started off great, I started hearing songs again that I really enjoyed! But then another issue came up...

THE PROBLEM, PART 2
Some of these songs hadn't been listened to in 2+ months for a reason -- I didn't really like them all that much, or was already sick of them. As I continued to listen to the playlist, when I skipped those songs, they remained in the list, while the songs I liked automatically got booted off the list since they had now been played in the past 2 months. The result is that as time went by, the list became increasingly populated by songs I didn't want to listen to.

THE SOLUTION, PART 2
Well, lo and behold, there is another parameter I can use in iTunes to fix this!

-Songs that have been skipped at least once in the past month (removes songs I don't like, but allows them to return to the list in a month's time in case my taste changes by then).

Fantastic! The songs I skipped immediately got booted off the list. There are still two remaining problems, however...

THE PROBLEM, PARTS 3 & 4
I hadn't considered this until the playlist started cooking, but -- a lot of these songs haven't been played in 2+ months because they are Christmas-related songs! Whoops! There is no easy fix for this -- unless I go back and tag all those songs as belonging to the "Christmas" genre, and exclude that genre from the mix (which I may go and do later).

And then there's the biggest problem, really -- what to do with those songs that this playlist has allowed me to rediscover and enjoy? By virtue of being played, they are now immediately off the playlist! Is there another smart playlist I can create to capture them? This one I don't know how to answer. There may be a way to create a hybrid of songs that appeared on this and also were recently played, but I haven't figured it out yet.

Interestingly, iTunes offers several default smart playlists (recently added, most played, etc.) -- it'd be interesting to see if they expanded their default lists to include some similar concepts. Perhaps sparing users the work I just went through. They have made efforts with their Genius tool to expand your listening (which can also lead to expanding your buying), but I bet there's more that can be done.