I suspect it is because of the level of complexity of the program now with trying to support so many features. It used to just be a music player. Now it is a music player, a movie player, an interface for a store, an interface between computers and multiple formats of igadgets. Unfortunately they included it all in one package so if one thing needs tweaking you need to replace the whole thing. With more things in there, the more likely it is something will need tweaking.
As for resolving your particular issue, it's hard to say. If it's something only you are seeing then, frankly, it's not worth their time. Or it may be something they cannot reproduce. Each computer configuration is unique. If it's a feature request, then again they probably have to decide if there is enough interest to put it in.
By the way, you posted in the "Older Hardware" forum which usually means truly ancient Mac equipment, not iTunes for Windows which is where this should have been posted.