This isn't an answer to your specific problem -- it's another way to approach itunes that may be of help.
I tend to have long playlists, on the basis that I want to leave my phone in my pocket while working. (I'm a tree farmer = endless hours of transplanting and weeding. my iPhone keeps me at least near the borders of sanity) If I do something once, I figure I will want that list again later.
The computer version has extensive controls in smart playlists, and they update live.
I use this a lot, and have many lists like "Christmas 3 star" where 'genre = christmas, and rating greater than **.
A list called "On trial" where rating = no stars, and play count < 6, limit to 50 songs. At the end of a cycle of this I can go through and give some of them ratings. As I do so they vanish from that list. 1* means it's destined for the scrap heap. 3 * will usually put it on one of my lists based on genre.
You can make smart lists based on words in your notes. So, for example, if Bach's "Jesu, Joy of Man's desire" is both classical and christmas, you can leave it's genre as classical, but add the word Christmas to the notes. Then modify your smart list to add the condition "or notes contains 'christmas' (Hold option down when clicking + to make nested rules. I hate hidden controls....)
A song can be on multiple lists without taking up extra space. So for example, I have a Simon & Garfunkle 3* list, and I have a Folk 4 * list. Bridge over troubled water would be on both lists, but stored only once.
In addition, there are rafts of itunes applescripts for manipulating your library, moving meta data, redoing artists to standard formats, etc.