Joden -
First, this is a user forum and it is not an appropriate place to post open challenges to the Cakewalk development staff. This is not a place where you can expect to make a direct communication with these folks.
Second, My experience is that the bakers do take action on properly formulated problem reports. They do have to prioritize them and one of the considerations that they have to make is how many people are affected by a problem. Frankly, I can think of a dozen or more items that I would like them to address before wasting time on Play List functionality. I would be surprised if there are more than a dozen users who even know about it.
Try making a case for how usable the feature is (when working as you expect it to). Explain how you think it should work (backed up by their documentation where possible). This does appear to be something that would be cool for sequencing a live show (lights, backing synths, etc) but you will probably need to convince Noel that he isn't spending his programming resources to fix a feature that only you (and possibly three other people) are going to use.
The bakers have fixed problems that I have reported (nearly a dozen), so I know that the process can work. You just need to find a way to get engaged in the solution instead of whining about something that nobody else cares about.
Glen